Researchers Database

OKUJIMA, Tetsuo

    Graduate School of Science and Engineering Engineering for Production and Environment Associate Professor
Last Updated :2020/10/13

Researcher Information

Degree

  • Doctor(Science)(Tohoku University)

J-Global ID

Research Interests

  • 有機薄膜太陽電池   organic field effect transistor   azulene   phthalocyanine   porphyrin   aromatic compound   organic synthesis   構造有機化学   

Research Areas

  • Life sciences / Bioorganic chemistry
  • Nanotechnology/Materials / Structural/physical organic chemistry

Academic & Professional Experience

  • 2011/01 - Today  Ehime UniversityGraduate School of Science and EngineeringAssociate Professor
  • 2015/10 - 2016/09  KU LeuvenProf. Wim Dehaen Groupvisiting research associate
  • 2007/04 - 2010/12  Ehime UniversityGraduate School of Science and EngineeringAssistant Professor
  • 2006/04 - 2007/03  Ehime UniversityLecturer
  • 2006/04 - 2007/03  Ehime UniversityGraduate School of Science and EngineeringAssistant Professor
  • 2002/10 - 2006/03  Ehime UniversityFaculty of ScienceAssistant Professor
  • 2002/04 - 2002/09  Tohoku University大学院理学研究科化学専攻Technical assistant

Association Memberships

  • Society of Porphyrins & Phthalocyanines   基礎有機化学会   THE JAPAN SOCIETY OF APPLIED PHYSICS   THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY   日本化学会   The Chemical Society of Japan   

Published Papers

  • Hidemitsu Uno, Kota Muramatsu, Shogo Hiraoka, Hiroyuki Tahara, Mako Hirose, Eidai Tamura, Tatsumi Shiraishi, John Mack, Nagao Kobayashi, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase
    Chemistry – A European Journal 26 (25) 5701 - 5708 0947-6539 2020/05 [Peer-reviewed]
     Scientific journal
  • Tetsuo Okujima, Hayato Inaba, Shigeki Mori, Masayoshi Takase, Hidemitsu Uno
    Journal of Porphyrins and Phthalocyanines 24 (01n03) 394 - 400 1088-4246 2020/01 [Peer-reviewed]
     Scientific journal 
    A ring-contracted carbaporphyrin, azulitriphyrin(2.1.1), was synthesized via intramolecular McMurry coupling reaction. Absorption, NMR spectra and NICS calculations of protonated azulitriphyrin(2.1.1) revealed its Hückel aromatic character as a 14[Formula: see text] porphyrinoid.
  • Taku Shoji, Sho Takagaki, Yukino Ariga, Akari Yamazaki, Mutsumi Takeuchi, Akira Ohta, Ryuta Sekiguchi, Shigeki Mori, Tetsuo Okujima, Shunji Ito
    Chemistry: A European Journal (Weinheim an der Bergstrasse, Germany) 26 (9) 1931 - 1935 2019/11 [Peer-reviewed]
     
    In this paper, we describe an efficient and atom-economical synthesis of highly functionalized pyrroles, pentafulvenes, and pyrrolopyridines by [2+2] cycloaddition-retroelectrocyclization of N-substituted propargylamines with tetracyanoethylene, followed by the treatment of the resulting tetracyanobutadiene derivatives with silica gel. In this reaction, silica gel plays an important role to promote the intramolecular cyclization to afford the heterocyclic products from the tetracyanobutadiene intermediates. The products were obtained selectively depending on the substituent on the nitrogen atom of the starting propargylamines.
  • Tetsuo Okujima, Yusuke Hashimoto, Tomoya Furuta, Ritsuko Yamanaka, Guangnan Jin, Saika Otsubo, Shinji Aramaki, Shigeki Mori, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    Bulletin of the Chemical Society of Japan 92 (8) 1370 - 1378 0009-2673 2019/08 [Peer-reviewed]
     Scientific journal
  • Taniyuki Furuyama, Tetsuo Okujima, Kota Muramatsu, Yuichi Takahashi, Akihiro Mikami, Tomoteru Fukumura, Shigeki Mori, Takahiro Nakae, Masayoshi Takase, Hidemitsu Uno, Nagao Kobayashi
    European Journal of Organic Chemistry 2019 (20) 3224 - 3235 1434-193X 2019/06 [Peer-reviewed]
     Scientific journal 
    © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim A series of free-base and phosphorus(V) complexes of tetrabenzoporphyrin (TBP) and some phosphorus(V) porphyrins containing four or eight phenyl groups on the periphery have been synthesized and characterized by X-ray crystallography, electronic absorption, and magnetic circular dichroism (MCD) spectroscopy, together with quantum chemical calculations. All phosphorus TBP and meso-tetraphenyl porphyrin complexes adapted ruffled conformations due to the small P(V) ion, although the Zn(II)TBPs containing eight phenyl (Φ) groups at the so-called β and α positions showed planar and saddled structures in the solid state, due to, respectively, marginal or severe steric hindrance between the neighboring Φ groups. All P(V)TBPs showed the Soret and Q bands beyond 450 and 700 nm, respectively, which are some of the longest wavelengths exhibited by metallated TBPs reported to date. Of the eight Φ group-substituted P(V)TBPs, those substituted at α positions always showed absorption bands at longer wavelengths than those at β positions, which was reproduced by calculated absorption spectra. The Soret band positions of meso-tetraphenylated P(V) species without fused benzo-groups (ca. 430–440 nm) were also some of the longest among metalloporphyrins of this type.
  • Synthesis of azuleno[2,1-b]thiophenes by cycloaddition of azulenylalkynes with elemental sulfur and their structural, optical and electrochemical properties
    Shoji, Taku, Miura, Kota, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Endo, Yuya, Nagahata, Tatsuki, Mori, Shigeki, Okujima, Tetsuo
    Org. Chem. Front. 6 (15) 2801 - 2811 2019/06 [Peer-reviewed]
     Scientific journal
  • Synthesis and Redox Properties of Pyrrole- and Azulene-Fused Azacoronene
    Sasaki, Yoshiki, Takase, Masayoshi, Okujima, Tetsuo, Mori, Shigeki, Uno, Hidemitsu
    Organic Letters 21 (6) 1900 - 1903 2019/03 [Peer-reviewed]
     Scientific journal
  • Di(acenaphtho)BODIPYs and Dipyrrins as Dyes With Deep-Red To NIR Absorptions
    Uno, Hidemitsu, Hirose, Mako, Honda, Takayuki, Mori, Shigeki, Takase, Masayoshi, Okujima, Tetsuo
    Bull. Chem. Soc. Jpn. 92 (5) 1001 - 1007 2019/02 [Peer-reviewed]
     Scientific journal
  • Oxidation Behavior of 1,3-Dihydrothieno[3,4-a]HPHAC
    Uno, Hidemitsu, Ishiwata, Misaki, Muramatsu, Kota, Takase, Masayoshi, Mori, Shigeki, Okujima, Tetsuo
    Bull. Chem. Soc. Jpn. 92 (5) 973 - 981 2019/02 [Peer-reviewed]
     Scientific journal
  • Synthesis of 6-Amino- and 6-Arylazoazulenes: Via Nucleophilic Aromatic Substitution and Their Reactivity and Properties
    Shoji, Taku, Sugiyama, Shuhei, Takeuchi, Mutsumi, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Yatsu, Tomoaki, Okujima, Tetsuo, Yasunami, Masafumi
    J. Org. Chem. 84 (3) 1257 - 1275 2019/01 [Peer-reviewed]
     Scientific journal
  • Tetsuo Okujima, Kota Muramatsu, Shigeki Mori, Masayoshi Takase, Hidemitsu Uno
    HETEROCYCLES 99 (2) 1434 - 1434 0385-5414 2019 [Peer-reviewed]
     Scientific journal
  • Synthesis of Azulenophthalimides by Phosphine-Mediated Annulation of 1,2-Diformylazulenes with Maleimides
    Shoji, Taku, Araki, Takanori, Iida, Nanami, Miura, Kota, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Okujima, Tetsuo
    Org. Chem. Front. 6 195 - 204 2018/11 [Peer-reviewed]
  • Kosuke Oki, Masayoshi Takase, Shigeki Mori, Akitoshi Shiotari, Yoshiaki Sugimoto, Keishi Ohara, Tetsuo Okujima, Hidemitsu Uno
    Journal of the American Chemical Society 140 (33) 10430 - 10434 0002-7863 2018/08 [Peer-reviewed]
     Scientific journal 
    Copyright © 2018 American Chemical Society. A core-expanded, pyrrole-fused azacoronene analogue containing two unusual N-doped heptagons was obtained from commercially available octafluoronaphthalene and 3,4-diethylpyrrole in two steps as a heteroatom-doped nonplanar nanographene. Full fusion with the formation of the tetraazadipleiadiene framework and the longitudinally twisted structure was unambiguously confirmed by single-crystal X-ray diffraction analysis. The edge-to-edge dihedral angle along the acene moiety was 63°. This electron-rich π-system showed four reversible oxidation peaks. Despite the nonplanar structure, the Hückel aromaticity owing to a peripheral π-conjugation in the dicationic state was concluded from the bond-length alternation and nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID) calculations.
  • Synthesis of 2-Methyl-1-azulenyl Tetracyanobutadienes and Dicyanoquinodimethanes: Substituent Effect of 2-Methyl Moiety on Azulene Ring toward the Optical and Electrochemical Properties
    Shoji, Taku, Miura, Kota, Araki, Takanori, Maruyama Akifumi, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Okujima, Tetsuo
    J. Org. Chem. 83 6690 - 6705 2018/05 [Peer-reviewed]
  • Chiral Discrimination and Manipulation of Individual Heptahelicene Molecules on Cu(001) by Noncontact Atomic Force Microscopy
    Shiotari, Akitoshi, Tanaka, Koichi, Nakae, Takahiro, Mori, Shigeki, Okujima, Tetsuo, Uno, Hidemitsu, Sakaguchi, Hiroshi, Sugimoto, Yoshiaki
    J. Phys. Chem. C 122 (9) 4997 - 5003 2018/02 [Peer-reviewed]
  • Taku Shoji, Shuhei Sugiyama, Kota Miura, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Shigeki Mori, Tetsuo Okujima
    Heterocycles 97 (2) 1068 - 1081 0385-5414 2018 [Peer-reviewed]
     Scientific journal 
    © 2018 The Japan Institute of Heterocyclic Chemistry – 3-Substituted 2-amino-1-cyanoazulene derivatives were prepared by the reaction of 2H-cyclohepta[b]furan-2-ones with malononitrile in the presence of triethylamine as a base. The great influence of the substituent at their 3-position on the reactivity to form the 2-aminoazulene derivatives was revealed. The intramolecular charge transfer (ICT) characters of 2-amino-1-cyano-3-vinylazulenes were investigated by UV/Vis spectroscopy and theoretical calculations. The structure of compounds 13b and 14b was clarified by single crystal X-ray analysis.
  • Tetsuo Okujima, Toshiki Abe, Shigeki Mori, Takahiro Nakae, Hidemitsu Uno
    HETEROCYCLES 96 (7) 1239 - 1239 0385-5414 2018 [Peer-reviewed]
     Scientific journal
  • Hidemitsu Uno, Takayuki Honda, Manami Kitatsuka, Shogo Hiraoka, Shigeki Mori, Masayoshi Takase, Tetsuo Okujima, Takahiro Nakae
    RSC Advances 8 (25) 14072 - 14083 2018 [Peer-reviewed]
     Scientific journal 
    © 2018 The Royal Society of Chemistry. Benzene-fused bis(acenaphthoBODIPY)s prepared by retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused precursors showed strong absorption bands in the near-infrared region and very weak absorptions in the visible region.
  • Molecular Transformation of 2-Methylazulenes: An Efficient and Practical Synthesis of 2-Formyl- and 2-Ethynylazulenes
    Shoji, Taku, Araki, Takanori, Iida, Nanami, Kobayashi, Yoshiaki, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Mori, Shgeki, Okujma, Tetsuo, Yasunami, Masafumi
    Eur. J. Org. Chem. 2018 1148 - 1157 2018/01 [Peer-reviewed]
  • Synthesis of Azulene-Substituted Benzofurans and Isocoumarins via Intramolecular Cyclization of 1-Ethynylazuelenes, and Their Structural and Optical Properties
    Shoji, Taku, Tanaka, Miwa, Takagaki, Sho, Miura Kota, Ohta, Akira, Sekiguchi, Ryuta, Ito, Shunji, Mori, Shgeki, Okujma, Tetsuo
    Org. Biomol. Chem. 16 480 - 489 2017/12 [Peer-reviewed]
  • Synthesis of Azulene-Substituted Tetraarylpyrroles by Reaction of 1-Azulenyl Ketones with Benzoin and Ammonium Acetate
    Shoji, Taku, Takagaki Sho, Tanaka, Miwa, Araki, Takanori, Sugiyama, Shuhei, Sekiguchi, Ryuta, Ohta, Akira, Ito, Shunji, Okujima, Tetsuo
    Heterocycles 94 1870 - 1883 2017/09 [Peer-reviewed]
  • Akitoshi Shiotari, Takahiro Nakae, Kota Iwata, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroshi Sakaguchi, Yoshiaki Sugimoto
    Nature Communications 8 16089/1 - 8 2017/07 Scientific journal 
    Controlling the structural deformation of organic molecules can drive unique reactions that cannot be induced only by thermal, optical or electrochemical procedures. However, in conventional organic synthesis, including mechanochemical procedures, it is difficult to control skeletal rearrangement in polycyclic aromatic hydrocarbons (PAHs). Here, we demonstrate a reaction scheme for the skeletal rearrangement of PAHs on a metal surface using high-resolution noncontact atomic force microscopy. By a combination of organic synthesis and on-surface cyclodehydrogenation, we produce a well-designed PAH - diazuleno[1,2,3-cd:1′,2′,3′-fg]pyrene - adsorbed flatly onto Cu(001), in which two azuleno moieties are highly strained by their mutual proximity. This local strain drives the rearrangement of one of the azuleno moieties into a fulvaleno moiety, which has never been reported so far. Our proposed thermally driven, strain-induced synthesis on surfaces will pave the way for the production of a new class of nanocarbon materials that conventional synthetic techniques cannot attain.
  • Taku Shoji, Shuhei Sugiyama, Takanori Araki, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Shigeki Mori, Tetsuo Okujima, Masafumi Yasunami
    Organic & biomolecular chemistry 15 (18) 3917 - 3923 2017/05 [Peer-reviewed]
     
    The SNAr reaction of 2-chloroazulene derivative 1 with ethoxycarbonyl groups at the 1,3-positions of the azulene ring with several amines afforded the corresponding 2-aminoazulenes 3-9 in excellent yields. 2-Chloroazulene (2) without the electron-withdrawing groups reacted with highly nucleophilic cyclic amines (i.e., morpholine, piperidine and pyrrolidine) under the high-temperature conditions in a sealed tube to produce the corresponding 2-aminoazulenes 10-12 in good yields. 2-Aminoazulenes 10-14 without the electron-withdrawing groups were also obtained in good yields by the treatment of compounds 3-7 with 100% H3PO4, but in the cases of the reaction of 8 and 9 with a secondary amine function, the decomposition of the products resulted. The synthesis of 2-arylazoazulenes 15-18 was also established via the SNAr reaction of 1 with arylhydrazines. The optical and electrochemical properties of the 2-arylazoazulene derivatives were examined by UV/Vis spectroscopy, theoretical calculations and voltammetric experiments.
  • Taku Shoji, Shuhei Sugiyama, Takanori Araki, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Shigeki Mori, Tetsuo Okujima, Masafumi Yasunami
    Organic & biomolecular chemistry 15 (18) 3917 - 3923 1477-0520 2017/05 
    The SNAr reaction of 2-chloroazulene derivative 1 with ethoxycarbonyl groups at the 1,3-positions of the azulene ring with several amines afforded the corresponding 2-aminoazulenes 3-9 in excellent yields. 2-Chloroazulene (2) without the electron-withdrawing groups reacted with highly nucleophilic cyclic amines (i.e., morpholine, piperidine and pyrrolidine) under the high-temperature conditions in a sealed tube to produce the corresponding 2-aminoazulenes 10-12 in good yields. 2-Aminoazulenes 10-14 without the electron-withdrawing groups were also obtained in good yields by the treatment of compounds 3-7 with 100% H3PO4, but in the cases of the reaction of 8 and 9 with a secondary amine function, the decomposition of the products resulted. The synthesis of 2-arylazoazulenes 15-18 was also established via the SNAr reaction of 1 with arylhydrazines. The optical and electrochemical properties of the 2-arylazoazulene derivatives were examined by UV/Vis spectroscopy, theoretical calculations and voltammetric experiments.
  • Taku Shoji, Daichi Nagai, Miwa Tanaka, Takanori Araki, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Shigeki Mori, Tetsuo Okujima
    Chemistry (Weinheim an der Bergstrasse, Germany) 23 (21) 5126 - 5136 0947-6539 2017/04 
    Synthesis of 2-aminofuran derivatives with an azulene or N,N-dimethylanilino substituent was established by the formal [2+2] cycloaddition-retroelectrocyclization of 3-(1-azulenyl or N,N-dimethylanilino)-2-propyn-1-ols with tetracyanoethylene, followed by intramolecular nucleophilic addition to the initially formed tetracyanobutadiene moiety of the internal hydroxyl group that come from 2-propyn-1-ol. The reaction proceeds under mild conditions with short reaction period. The products of the reaction are readily available through a simple purification procedure. 2-Aminofuran derivatives obtained by this reaction could be converted into 6-aminofulvene derivatives upon reaction with various amines. The structures of 2-aminofuran and 6-aminopentafulvene with a N,N-dimethylanilino substituent were confirmed by single-crystal X-ray structural analysis.
  • Taku Shoji, Takanori Araki, Shuhei Sugiyama, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Tetsuo Okujima, Kozo Toyota
    The Journal of organic chemistry 82 (3) 1657 - 1665 0022-3263 2017/02 
    Tetrathiafulvalene (TTF) derivatives with 2-azulenyl substituents 5-11 were prepared by the palladium-catalyzed direct arylation reaction of 2-chloroazulenes with TTF in good yield. Photophysical properties of these compounds were investigated by UV-vis spectroscopy and theoretical calculations. Redox behavior of the novel azulene-substituted TTFs was examined by using cyclic voltammetry and differential pulse voltammetry, which revealed their multistep electrochemical oxidation and/or reduction properties. Moreover, these TTF derivatives showed significant spectral change in the visible region under the redox conditions.
  • Shogo Hiraoka, Hiroyuki Tahara, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase, Takahiro Nakae, Hidemitsu Uno
    TETRAHEDRON 73 (7) 957 - 963 0040-4020 2017/02 [Peer-reviewed]
     Scientific journal 
    Parikh-Doering oxidation of diethyl 9-hydroxy-2,6-dimethy1-4,8-dihydro-4,8-methanopyrrol[3,4-f]isoindole-1,7-dicarboxylate produced diethyl 9-oxo-2,6-dimethy1-4,8-dihydro-4,8-methanopyrrol[3,44] isoindole-1,7-dicarboxylate. This carbonyl derivative spontaneously underwent cheletropic extrusion of carbon monoxide, producing diethyl 2,6-dimethylpyrrol[3,4-f]isoindole-1,7-dicarboxylate, which showed 14 pi-electronic aromaticity on the whole five-six-five ring system. (C) 2017 Elsevier Ltd. All rights reserved.
  • Kazunari Tagawa, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase, Hidemitsu Uno
    TETRAHEDRON 73 (6) 794 - 801 0040-4020 2017/02 [Peer-reviewed]
     Scientific journal 
    The protonation behavior of bicyclo[2.2.2]octadiene (BCOD)-fused thiaporphyrin and thiabenzoporphyrin was examined by titration with trifluoroacetic acid. Neutral, monorotonated, and diprotonated species of thiaporphyrins were easily detected by UV-vis spectral measurement. The first (K-1) and second (K-2) equilibrium constants were found to be K-1 = 520 and K-2 approximate to 7.1 for BCOD-fused thiaporphyrin and K-1 = 1.4 x 10(4) and K-2 approximate to 1.4 for thiabenzoporphyrin. The difference between K-1 and K-2 values of thiaporphyrins is larger than that observed for porphyrins (N-4-porphyrins). The main contributing conjugation pathways for thiaporphyrins in both protonated species were investigated by NICS and AICD quantum calculations using their atomic geometries obtained by X-ray structural analysis. The 18 pi-conjugation pathways of the neutral, monoprotonated, and diprotonated species thiaporphyrins were found to contain 18, 19, and 20 atoms, respectively. Results of H-1 NMR studies also support the major contributing pathways. (C) 2016 Elsevier Ltd. All rights reserved.
  • Kosuke Oki, Kazunari Tagawa, Shigeki Mori, Masayoshi Takase, Tetsuo Okujima, Hidemitsu Uno
    CHEMISTRY LETTERS 46 (2) 243 - 244 0366-7022 2017/02 [Peer-reviewed]
     Scientific journal 
    A cyclophane composed of diethanoanthracene (DEA)-fused dipyrrole and tetrafluorobenzene was synthesized by one-pot aromatic nucleophilic substitution (SNAr). Reflecting the fixed angle of DEA-fused dipyrrole, X-ray single-crystal structure analysis of the cyclophane revealed its rice-ball-shaped structure.
  • Shogo Hiraoka, Hiroyuki Tahara, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase, Takahiro Nakae, Hidemitsu Uno
    TETRAHEDRON 73 (7) 957 - 963 0040-4020 2017/02 Scientific journal 
    Parikh-Doering oxidation of diethyl 9-hydroxy-2,6-dimethy1-4,8-dihydro-4,8-methanopyrrol[3,4-f]isoindole-1,7-dicarboxylate produced diethyl 9-oxo-2,6-dimethy1-4,8-dihydro-4,8-methanopyrrol[3,44] isoindole-1,7-dicarboxylate. This carbonyl derivative spontaneously underwent cheletropic extrusion of carbon monoxide, producing diethyl 2,6-dimethylpyrrol[3,4-f]isoindole-1,7-dicarboxylate, which showed 14 pi-electronic aromaticity on the whole five-six-five ring system. (C) 2017 Elsevier Ltd. All rights reserved.
  • Shoji, Taku, Maruyama, Mitsuhisa, Maruyama, Akifumi, Nagai, Daichi, Tanaka, Miwa, Sekiguchi, Ryuta, Ito, Shunji, Okujima, Tetsuo
    Heterocycles 95 (1) 353 - 369 2017 [Peer-reviewed]
     Scientific journal
  • Hidemitsu Uno, Kazunari Tagawa, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase, Takahiro Nakae
    Bulletin of the Chemical Society of Japan 90 (12) 1375 - 1381 1348-0634 2017 [Peer-reviewed]
     Scientific journal 
    In this study, a benzene-fused bis(thiaporphyrin) was synthesized by the retro-DielsAlder reaction of a bicyclo[2.2.2]- octadiene (BCOD)-fused bis(thiaporphyrin) precursor. This precursor was prepared by the double [3+1] porphyrin synthesis of the BCOD-fused dipyrrole with thiatripyrrane. The ultravioletvisible (UVvis) spectrum of benzene-fused bis- (thiaporphyrin) in dichloromethane was extremely different from that of the corresponding benzene-fused bis(porphyrin). In contrast, extremely similar spectra were obtained in the presence of trifluoroacetic acid. The similar electronic structures in the protonated states were supported by X-ray analysis and time-dependent density-functional theory (TD-DFT) calculations.
  • Shoji, Taku, Takagaki, Sho, Tanaka, Miwa, Araki, Takanori, Sugiyama, Shuhei, Sekiguchi, Ryuta, Ohta, Akira, Ito, Shunji, Okujima, Tetsuo
    Heterocycles 94 (10) 1870 - 1883 0385-5414 2017 Scientific journal 
    © 2017 The Japan Institute of Heterocyclic Chemistry. Tetraarylpyrroles with a 1-azulenyl substituent were prepared by the reaction of 1-azulenyl ketones, which have various aryl-substituents at their á-position, with benzoin in the presence of ammonium acetate as a nitrogen source of the pyrrole ring. Optical property of the tetraarylpyrroles obtained by the reaction was clarified by UV/Vis spectroscopy and/or time-dependent density functional theory (TD-DFT) calculations.
  • Tetsuo Okujima, John Mack, Jun Nakamura, Gugu Kubheka, Tebello Nyokong, Hua Zhu, Naoki Komobuchi, Noboru Ono, Hiroko Yamada, Hidemitsu Uno, Nagao Kobayashi
    CHEMISTRY-A EUROPEAN JOURNAL 22 (41) 14730 - 14738 0947-6539 2016/10 [Peer-reviewed]
     Scientific journal 
    A series of porphyrins fused with acenaphthylene, phenanthroline, and benzofluoranthene polycyclic aromatic rings were prepared by means of a 3+1 porphyrin synthesis approach and subsequent retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused precursors. Analysis of the magnetic circular dichroism spectra and the results of time-dependent DFT calculations are used to identify the reasons for the trends observed in the wavelengths and relative intensities of the Q bands of the products. Michl's perimeter model is used as a conceptual framework to explain the changes in the relative energies of the frontier -molecular orbitals.
  • Kazunari Tagawa, Shigeki Mori, Masayoshi Takase, Tetsuo Okujima, Ichiro Hisaki, Hidemitsu Uno
    TETRAHEDRON LETTERS 57 (36) 4079 - 4081 0040-4039 2016/09 [Peer-reviewed]
     Scientific journal 
    In this study, hexagonal shape-persistent cyclophane with D-2h symmetry and rigid dihedral angles was obtained through the key SNAr reaction of perfluorobenzene moieties and dipyrroles. The X-ray analysis of the compound thus obtained revealed a hexagonal macrocyclic structure with D-2h symmetry due to the dihedral angles of 120 degrees and double 120 degrees for bicyclo[2.2.2]octadiene:fused dipyrrole and syn-diethanotetrahydroanthracene-fused dipyrrole, respectively. (C) 2016 Elsevier Ltd. All rights reserved.
  • Tetsuo Okujima, Hiroki Matsumoto, Shigeki Mori, Takahiro Nakae, Masayoshi Takase, Hidemitsu Uno
    TETRAHEDRON LETTERS 57 (29) 3160 - 3162 0040-4039 2016/07 [Peer-reviewed]
     Scientific journal 
    A complex of Cyclo[8]pyrrole with polyoxometalate, POM-to-Rings, was synthesized by anion exchange from cyclo[8]pyrrole sulfate. X-ray crystallographic study revealed the double-decker structure. (C) 2016 Elsevier Ltd. All rights reserved.
  • Tetsuo Okujima, Chie Ando, Saurabh Agrawal, Hiroki Matsumoto, Shigeki Mori, Keishi Ohara, Ichiro Hisaki, Takahiro Nakae, Masayoshi Takase, Hidemitsu Uno, Nagao Kobayashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 138 (24) 7540 - 7543 0002-7863 2016/06 [Peer-reviewed]
     Scientific journal 
    An acenaphthylene-fused cyclo[10]pyrrole 1b was selectively synthesized via an oxidative coupling reaction of the corresponding 2,2'-bipyrrole with the appropriate dianion template, croconate anion. The structure of 1b as the isolated largest cyclo[n]pyrrole was elucidated by X-ray crystallographic analysis. The absorption spectrum exhibited a markedly red-shifted, intensified L band at 1982 nm, which was interpreted by application of Michl's perimeter and Gouterman's 4-orbital models, supported by magnetic circular dichroism (MCD) data and theoretical calculations.
  • Synthesis and Properties of (3-Phenyl-1-azulenyl)tetracyanobetadienes and Tris(aryltetracyanobetadiene)s Connected with 1,3,5-Tri(1-azulenyl)benzene Core
    Shoji, Taku, Maruyama, Akifumi, Tanaka, Miwa, Nagai, Daichi, Shimomura, Erika, Fujimori, Kunihide, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo, Yasunami, Masafumi (th
    Chemistry Select 1 49 - 56 2016 [Peer-reviewed]
  • Shoji, Taku, Miyashita, Kanami, Araki, Takanori, Tanaka, Miwa, Maruyama, Akifumi, Sekiguchi, Ryuta, Ito, Shunji, Okujima, Tetsuo
    Synthesis-Stuttgart 48 (15) 2438 - 2448 0039-7881 2016 [Peer-reviewed]
     Scientific journal 
    The synthesis of 1,2′-biazulenes was established by palladium-catalyzed homocoupling reactions of the corresponding 1-haloazulenes in the presence of ferrocene. The optical properties of the novel 1,2′-biazulenes were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behaviors of 1,2′-biazulenes were also examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV).
  • Taku Shoji, Akifumi Maruyama, Takanori Araki, Shunji Ito, Tetsuo Okujima
    Organic & biomolecular chemistry 13 (40) 10191 - 7 2015/10 [Peer-reviewed]
     Scientific journal 
    Preparation of 2- and 6-thienylazulene derivatives was established by the palladium-catalyzed direct cross-coupling reaction of 2- and 6-haloazulenes with the corresponding thiophene derivatives in good yield. Several thienylazulene derivatives were also used in the reaction with 2-chloroazulene derivatives in the presence of the palladium-catalyst to afford the thiophene derivatives with two azulene functions in good yield.
  • Shoji, Taku, Maruyama, Akifumi, Yaku, Chisa, Kamata, Natsumi, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo
    Chem. Eur. J. 21 402 - 409 0947-6539 2015/01 [Peer-reviewed]
     Scientific journal 
    © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Aryl-substituted 1,1,4,4-tetracyano-1,3-butadienes (FcTCBDs) and bis(1,1,4,4-tetracyanobutadiene)s (bis- FcTCBDs), possessing a ferrocenyl group on each terminal, were prepared by the reaction of a variety of alkynes with tetracyanoethylene (TCNE) in a [2+2] cycloaddition reaction, followed by retro-electrocyclization of the initially formed [2+2] cycloadducts (i.e., cyclobutene derivatives). The characteristic intramolecular charge transfer (ICT) between the donor (ferrocene) and acceptor (TCBD) moieties were investigated by using UV/Vis spectroscopy. The redox behaviors of FcTCBDs and bis-FcTCBDs were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their properties of multi-electron transfer depending on the number of ferrocene and TCBD moieties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions.
  • Synthesis and Properties of (3-Phenyl-1-azulenyl)tetracyanobetadienes and Tris(aryltetracyanobetadiene)s Connected with 1,3,5-Tri(1-azulenyl)benzene Core
    Shoji, Taku, Maruyama, Akifumi, Tanaka, Miwa, Nagai, Daichi, Shimomura, Erika, Fujimori, Kunihide, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo, Yasunami, Masafumi (th
    Chemistry Select 1 49 - 56 2015 [Peer-reviewed]
     Scientific journal
  • Shoji, Taku, Kamata, Natsumi, Maruyama, Akifumi, Ito, Shunji, Okujima, Tetsuo
    Bulletin of the Chemical Society of Japan 88 (9) 1338 - 1346 2015 [Peer-reviewed]
     Scientific journal
  • Shoji, Taku, Maruyama, Akifumi, Shimomura, Erika, Nagai, Daichi, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo
    European Journal of Organic Chemistry (9) 1979 - 1990 2015 [Peer-reviewed]
     Scientific journal
  • Hidemitsu Uno, Mitsunori Nakamura, Kazuki Jodai, Shigeki Mori, Tetsuo Okujima
    HETEROCYCLES 90 (2) 1158 - 1167 0385-5414 2015/01 [Peer-reviewed]
     Scientific journal 
    4,8-Dihydropyrrol[3,4-f]isoindole was prepared from 4,7-dihydroisoindole based on the modified Barton-Zard reaction. Addition of phenylsulfenyl chloride followed by oxidation and dehydrochlorination gave phenylsulfonyldihydroisoindole, which underwent the smooth reaction with an isocyanoacetate under basic conditions to give 4,8-dihydropyrrol[3,4-f]isoindole-1,5- and 1,7-dicarboxylates in good yields. The pyrrolisoindole was successfully converted to the benzene-fused bisBODIPY, absorption maximum of which was 758 nm.
  • Hidemitsu Uno, Kazunari Tagawa, Hajime Watanabe, Naoki Kawamoto, Mina Furukawa, Tetsuo Okujima, Shigeki Mori
    Chemical Science of Electron Systems 17 - 36 2015/01 In book 
    Oligoporphyrins with a large fused π-electron system were successfully synthesized by the fusion of porphyrin chromophores with polycyclic aromatic hydrocarbons (PAHs). Oligoporphyrins fused with benzene units and zinc diporphyrins fused with PAHs were prepared and their electronic properties were examined. Electronic spectra showed strong absorption in the red to near-infrared (NIR) region. Not only the absorption maxima but also the number of absorption bands was affected by the fusion mode of the porphyrin chromophores. In the UV-vis spectra of the oligoporphyrins, three major absorption bands corresponding to Soret and Q bands were observed. A linearly fused trizinc triporphyrin with two benzene moieties showed strong Q-band absorption at 680nm, while split Q-band absorptions at 663 and 674nm were observed in the L-shaped triporphyrin. Preparation based on the retro-Diels-Alder reaction of the precursors with a bicyclo[2.2.2]octadiene skeleton did not give naphthacene- and pentacene-fused diporphyrins but instead gave naphthalene-, anthracene-, and chrysene-fused diporphyrins. In the chrysene-fused diporphyrin, the absorption maximum in the Q band was 624nm, which was similar to that of naphthalene-fused diporphyrin.
  • Taku Shoji, Mitsuhisa Maruyama, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota
    Chemistry (Weinheim an der Bergstrasse, Germany) 20 (37) 11903 - 12 0947-6539 2014/09 
    1,3-Bis(azulenylethynyl)azulene derivatives 9-14 have been prepared by palladium-catalyzed alkynylation of 1-ethynylazulene 8 with 1,3-diiodoazulene 1 or 1,3-diethynylazulene 2 with the corresponding haloazulenes 3-7 under Sonogashira-Hagihara conditions. Bis(alkynes) 9-14 reacted with tetracyanoethylene (TCNE) in a formal [2+2] cycloaddition-retroelectrocyclization reaction to afford the corresponding new bis(tetracyanobutadiene)s (bis(TCBDs)) 15-20 in excellent yields. The redox behavior of bis(TCBD)s 15-20 was examined by using CV and differential pulse voltammetry (DPV), which revealed their reversible multistage reduction properties under the electrochemical conditions. Moreover, a significant color change of alkynes 9-14 and TCBDs 15-20 was observed by visible spectroscopy under the electrochemical reduction conditions.
  • Tetsuo Okujima, Yoichi Shida, Keishi Ohara, Yuya Tomimori, Motoyoshi Nishioka, Shigeki Mori, Takahiro Nakae, Hidemitsu Uno
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 18 (8-9) 752 - 761 1088-4246 2014/08 Scientific journal 
    A series of O-chelated BODIPYs fused with aromatic rings such as benzene and acenaphthylene at beta,beta-positions was synthesized as a near-infrared dye. The photophysical properties were examined by UV-vis-NIR absorption and fluorescence measurement. Acenaphthylene-fused O-BODIPYs showed a intense absorption at 750-840 nm with the epsilon of 10(5) M-1.cm(-1). and a fluorescene emission at 770-850 nm with the high Phi value of 0.06-0.43.
  • Takahiro Nakae, Takashi Kikuchi, Shigeki Mori, Tetsuo Okujima, Toshihiro Murafuji, Hidemitsu Uno
    CHEMISTRY LETTERS 43 (4) 504 - 506 0366-7022 2014/04 Scientific journal 
    1,3-Bisarylated-2,2'-biazulene 1 and 1,1'-bisarylated-2,2'-biazulene 1' were obtained by the Suzuki-Miyaura crosscoupling reaction of 1,1',3,3'-tetrahalo-2,2'-biazulene 2 with 4-tert-butylphenylboronic acid (3b). The other two halogen atoms were reductively removed by hydrogenation under the same reaction conditions. The major regioisomer 1 was obtained with a selectivity of up to 94% (15:1) and a combined yield of 1 and 1' of up to 77%.
  • Tetsuo Okujima, Yoichi Shida, Keishi Ohara, Yuya Tomimori, Motoyoshi Nishioka, Shigeki Mori, Takahiro Nakae, Hidemitsu Uno
    J. Porphyrins Phthalocyanines 18 (8-9) 752 - 761 1099-1409 2014 [Peer-reviewed]
     Scientific journal 
    A series of O-chelated BODIPYs fused with aromatic rings such as benzene and acenaphthylene at β,β-positions was synthesized as a near-infrared dye. The photophysical properties were examined by UV-vis-NIR absorption and fluorescence measurement. Acenaphthylene-fused O-BODIPYs showed a intense absorption at 750–840 nm with the ε of 105 M-1.cm-1. and a fluorescence emission at 770–850 nm with the high Φ value of 0.06–0.43.


    Read More: http://www.worldscientific.com/doi/abs/10.1142/S1088424614500503
  • Shoji, Taku, Maruyama, Akifumi, Ito, Shunji, Okujima, Tetsuo, Yasunami, Masafumi, Higashi, Junya, Morita, Noboru
    Heterocycles 89 (11) 2588 - 2603 0385-5414 2014 Scientific journal 
    © 2014 The Japan Institute of Heterocyclic Chemistry. Preparation of 2-aryl- and 6-heteroarylazulenes 2-6 and 8-10 was established by the palladium-catalyzed cross-coupling reaction of the corresponding haloazulenes with lithium aryl- and heteroarylmagnesium ate complexes, which were readily prepared from the corresponding aryl and heteroaryl halides. The reaction of 2-6 and 8-10, except for 3 and 8, with pyridine in the presence of Tf 2 O, followed by treatment with KOH in MeOH afforded the corresponding 2-aryl- and 6-heteroaryl-1,3-di(4-pyridyl)azulenes 11-16 in good yields.
  • Shoji, Taku, Maruyama, Akifumi, Yamamoto, Atsuyo, Fujiwara, Yuki, Ito, Shunji, Okujima, Tetsuo, Morita, Noboru
    Chemistry Letters 43 (7) 1122 - 1124 0366-7022 2014 Scientific journal 
    Synthesis of 2,2'-diamino-1,1'-biazulene derivatives 5 and 911 was established by copper-catalyzed homocoupling reaction of the corresponding 2-aminoazulenes 3 and 68. The palladium-catalyzed cross-coupling reactions of 6,6'-dibromo- 1,1'-biazulene derivative 9 were also established under the SuzukiMiyaura and SonogashiraHagihara conditions. © 2014 The Chemical Society of Japan.
  • Tetsuo Okujima, Chie Ando, Shigeki Mori, Takahiro Nakae, Hiroko Yamada, Hidemitsu Uno
    HETEROCYCLES 88 (1) 417 - 424 0385-5414 2014/01 Scientific journal 
    Cyclo[8]pyrrole with eight 9,10-dihydroanthracene wings was synthesized by oxidative coupling of the corresponding 2,2'-bipyrrole in good yield. The molecular structure was determined by single crystal X-ray analysis. The three-dimensionally structured cyclo[8]pyrrole possessed a cavity created by a pair of slip-stacked cyclo[8]pyrroles.
  • Kazunari Tagawa, Shigeki Mori, Takahiro Nakae, Tetsuo Okujima, Hidemitsu Une
    HETEROCYCLES 88 (1) 453 - 462 0385-5414 2014/01 Scientific journal 
    The Hinsberg thiophene synthesis using 4,5,6,7-tetrahydro-4,7-ethanothiophene-5,6-dione and diethyl thiodiglycolate afforded a mixture of diethyl 4,8-dihydro-4,8-ethanobenzo[1,2-c;4,5-c']dithiophene-1,3-dicarboxylate and its dihydrate, although the yields were low. The latter dihydrate was converted to the former dithiophene in a good yield by the treatment with Ac2O and DMAP.
  • Shoji, Taku, Maruyama, Akifumi, Maruyama, Mitsuhisa, Ito, Shunji, Okujima, Tetsuo, Higashi, Junya, Toyota, Kozo, Morita, Noboru
    Bulletin of the Chemical Society of Japan 87 (1) 141 - 154 0009-2673 2014 Scientific journal 
    6-Methoxy- and 6-dimethylaminoazulenes with methylthio groups at the 1- or 1,3-positions have been prepared by electrophilic substitution of the corresponding azulenes with DMSO in the presence of acid anhydride, followed by treatment with Et 3 N. The products, 1-methylthioazulenes, reacted with Tf 2 O to afford the corresponding 1,1′-biazulene derivatives in moderate yields. The redox behavior of these azulene and 1,1′-biazulene derivatives was examined by cyclic voltammetry (CV), which revealed reversible electron transfers under electrochemical oxidation conditions. 6-Dimethylamino-1,3-bis(methylthio)azulenes with a heteroaiyl group at the 2-position were also prepared by the reaction of 6-dimethylamino-1,3- bis(methylthio)azulene with triflates of iV-containing heterocycles, i.e., pyridine, quinoline, isoquinoline, acridine, and 1,10-phenanthroline, followed by treatment with KOH in alcohols. © 2013 The Chemical Society of Japan.
  • Mitsunori Nakamura, Manami Kitatsuka, Kohtaro Takahashi, Toshi Nagata, Shigeki Mori, Daiki Kuzuhara, Tetsuo Okujima, Hiroko Yamada, Takahiro Nakae, Hidemitsu Uno
    ORGANIC & BIOMOLECULAR CHEMISTRY 12 (8) 1309 - 1317 1477-0520 2014 Scientific journal 
    Bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis(benzoborondipyrromethene)s (bisbenzoBODIPYs) bearing electron-withdrawing groups such as fluorine and cyano groups were prepared either by incorporating tetrafluoroisoindole moieties into BODIPY chromophores or by introducing cyano or ethoxycarbonyl groups at the 3,5-positions. The BCOD-fused bisbenzoBODIPYs were quantitatively converted to the corresponding benzene-fused bisbenzoBODIPYs by a retro-Diels-Alder reaction. The pi-fused bisbenzoBODIPYs were found to have intense absorption in the near-infrared region and not to have any strong absorption bands in the visible region. Moreover, the bisbenzoBODIPYs were stable under atmospheric conditions.
  • Taku Shoji, Mitsuhisa Maruyama, Erika Shimomura, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita
    The Journal of organic chemistry 78 (24) 12513 - 24 0022-3263 2013/12 
    Acetylene derivatives with an azulenyl group at both terminals have been prepared by palladium-catalyzed alkynylation under Sonogashira-Hagihara conditions. These alkynes reacted with tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane in a formal [2 + 2] cycloaddition-retroelectrocyclization reaction to afford the corresponding new tetracyanobutadienes (TCBDs) and dicyanoquinodimethanes (DCNQs), respectively, in excellent yields. Intramolecular CT absorption bands were found in the UV-vis spectra of the novel chromophores, and CV and DPV showed that they exhibited a reversible two-stage reduction wave, due to the electrochemical reduction of TCBD and DCNQ moieties. Color changes were also observed during the electrochemical reduction.
  • Daiki Kuzuhara, Zhaoli Xue, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Naoki Aratani, Hiroko Yamada
    Chemical Communications 49 (79) 8955 - 8957 1359-7345 2013/10 Scientific journal 
    Boron complexes of [14]triphyrins(2.1.1) were prepared from free-base [14]triphyrins(2.1.1) with phenylboron dichloride. The absorption spectrum of the meso-free β-alkyl-triphyrin boron complex in CH2Cl 2 showed a broad weak band at around 640 nm assigned to transition from B-phenyl to the triphyrin, while that of the meso-aryl benzotriphyrin boron complex showed only Soret and Q bands. © 2013 The Royal Society of Chemistry.
  • Tetsuo Okujima, Chie Ando, John Mack, Shigeki Mori, Ichiro Hisaki, Takahiro Nakae, Hiroko Yamada, Keishi Ohara, Nagao Kobayashi, Hidemitsu Uno
    CHEMISTRY-A EUROPEAN JOURNAL 19 (41) 13970 - 13978 0947-6539 2013/10 Scientific journal 
    An acenaphthylene-fused cyclo[8]pyrrole was synthesized by using an oxidative coupling reaction of the corresponding 2,2-bipyrrole. Two conformational isomers 1a and 1b were isolated, and their molecular structures were elucidated by X-ray crystallographic studies. The less-polar and lower-symmetry 1b isomer can be converted into the 1a isomer through a thermal ring flip. Application of the perimeter model developed by Michl to magnetic circular dichroism spectroscopic data and theoretical calculations demonstrate that there is a marked redshift of the near-IR absorption maxima relative to cyclo[8]isoindole because there is a significant stabilization of the LUMO due to the differing effects of a fused ring expansion with acenaphthylene and benzene moieties on the frontier molecular orbitals.
  • Kazuki Tanaka, Naoki Aratani, Daiki Kuzuhara, Sadaaki Sakamoto, Tetsuo Okujima, Noboru Ono, Hidemitsu Uno, Hiroko Yamada
    RSC Advances 3 (35) 15310 - 15315 2046-2069 2013/09 Scientific journal 
    We have synthesized 13,13′-(3,5-bis(trifluoromethyl)phenyl)-6, 6′-bipentacene from a soluble bispentacenequinone precursor. Bispentacene takes orthogonal conformation in the solid state and exhibits four reversible redox potentials. In addition, a tetracyanobipentacenequinodimethane was obtained for the first time from the pure bispentacenequinone. © The Royal Society of Chemistry 2013.
  • Noriyuki Hatae, Jun Nakamura, Tetsuo Okujima, Minoru Ishikura, Takumi Abe, Satoshi Hibino, Tominari Choshi, Chiaki Okada, Hiroko Yamada, Hidemitsu Uno, Eiko Toyota
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 23 (16) 4637 - 4640 0960-894X 2013/08 Scientific journal 
    9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 mu M. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity. (C) 2013 Elsevier Ltd. All rights reserved.
  • Zhaoli Xue, Daiki Kuzuhara, Shinya Ikeda, Yuka Sakakibara, Kei Ohkubo, Naoki Aratani, Tetsuo Okujima, Hidemitsu Uno, Shunichi Fukuzumi, Hiroko Yamada
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 (28) 7306 - 7309 1433-7851 2013/07 Scientific journal 
    A semiferrocene complex with a [14]triphyrin(2.1.1) (TriP) ligand has been synthesized. The structure and properties are characterized by X-ray crystallographic analysis, UV/Vis spectroscopy, and variable-temperature 1 H NMR spectroscopy. The Fe II and Fe III complexes are electrochemically reversible. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Tatsuya Aotake, Hiroshi Tanimoto, Hidekatsu Hotta, Daiki Kuzuhara, Tetsuo Okujima, Hidemitsu Uno, Hiroko Yamada
    Chemical Communications 49 (35) 3661 - 3663 1364-548X 2013/05 Scientific journal 
    The non-luminous precursor, 2-(1-pyrenyl)-9,10-dihydro-9,10- ethanoanthracene-11,12-dione, was photochemically converted to highly-fluorescent 2-(1-pyrenyl)anthracene quantitatively in solution and in the PMMA film and the fluorescence quantum yield of the acene in benzonitrile was as high as 0.99. © The Royal Society of Chemistry 2013.
  • Taku Shoji, Shunji Ito, Tetsuo Okujima, Noboru Morita
    Chemistry (Weinheim an der Bergstrasse, Germany) 19 (18) 5721 - 30 0947-6539 2013/04 
    1-, 2-, and 6-(Ferrocenylethynyl)azulene derivatives 10-16 have been prepared by palladium-catalyzed alkynylation of ethynylferrocene with the corresponding haloazulenes under Sonogashira-Hagihara conditions. Compounds 10-16 reacted with tetracyanoethylene (TCNE) in a [2+2] cycloaddition-cycloreversion reaction to afford the corresponding 2-azulenyl-1,1,4,4,-tetracyano-3-ferrocenyl-1,3-butadiene chromophores 17-23 in excellent yields. The redox behavior of the novel azulene chromophores 17-23 was examined by using cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, a significant color change was observed by visible spectroscopy under electrochemical reduction conditions.
  • Tatsuya Aotake, Yuko Yamashita, Tetsuo Okujima, Nobuhiko Shirasawa, Yukari Jo, Shigeo Fujimori, Hidemitsu Uno, Noboru Ono, Hiroko Yamada
    Tetrahedron Letters 54 (14) 1790 - 1793 0040-4039 2013/04 Scientific journal 
    Highly fluorescent naphthacene derivatives and their photoconvertible precursors were synthesized for irreversibly photo-responsive fluorescent molecules. The fluorescence quantum yields (Φf) of the precursors were less than 0.02, and the precursors can be converted to the highly fluorescent naphthacene derivatives (Φf = 0.67-0.70) quantitatively by photo-irradiation. © 2013 Elsevier Ltd. All rights reserved.
  • Zhaoli Xue, Daiki Kuzuhara, Shinya Ikeda, Tetsuo Okujima, Shigeki Mori, Hidemitsu Uno, Hiroko Yamada
    INORGANIC CHEMISTRY 52 (4) 1688 - 1690 0020-1669 2013/02 Scientific journal 
    Metalation of 6,13,20,21-tetrakis(4-methyl-phenyl)-22H-tribenzo[14]triphyrin(2.1.1) with PtCl2 gave a platinum(II) complex having a square-planar coordination structure with two pyrrolic nitrogen atoms and two chloride ions, with a saddle-shaped macrocycle. This platinum(II) complex was easily oxidized by air to an octahedral platinum(IV) complex coordinated by three pyrrolic nitrogen atoms as a tridentate monoanionic cyclic ligand and three chloride ions. When platinum(II) triphyrin was crystallized in air, an oxygen atom was incorporated between two alpha-carbon atoms of the pyrroles as an oxygen bridge to intercept the 14 pi aromatic system.
  • Shoji, Taku, Shimomura, Erika, Maruyama, Mitsuhisa, Ito, Shunji, Okujima, Tetsuo, Morita, Noboru
    European Journal of Organic Chemistry (5) 957 - 964 1434-193X 2013 Scientific journal 
    Ene-diyne systems possessing 1- and 2-azulenyl groups at the periphery were prepared by palladium-catalyzed cross-coupling reaction of 1- and 2-ethynylazulenes with 9-dibromomethylene-9H-fluorene and 9,10- bis(dibromomethylene)-9,10-dihydroanthracene or 2-iodoazulene with 9,10-bis(diethynylmethylene)-9,10-dihydroanthracene under Sonogashira-Hagihara conditions. The redox behavior of the ene-diyne compounds was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Moreover, a significant color change of the ene-diyne derivatives was observed with visible spectroscopy under electrochemical reduction conditions. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Aya Seike, Kaoru Yamagami, Yoshimasa Kakitani, Miki Kuwajima, Hiroki Uoyama, Shin-ichi Nagaoka, Takahiro Nakae, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno
    RSC ADVANCES 3 (9) 3006 - 3016 2046-2069 2013 Scientific journal 
    Ethyl 12-oxo-4,11-dihydro-4,11-ethanonaphth[2,3-f]isoindole-1-carboxylate (2) was prepared from 7-tert-butoxynorbornadiene and quantitatively converted to ethyl naphth[2,3-f]isoindole-1-carboxylate (3) by the thermal or photochemical cheletropic reaction. Ethyl naphth[2,3-f] isoindole-1-carboxylate (3) existed in a 2H-form both in solution and as a solid, and gradually dimerized to give a dianthradiazafulvalene derivative under aerobic conditions.
  • Daiki Kuzuhara, Yuka Sakakibara, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroko Yamada
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 (12) 3360 - 3363 1433-7851 2013 Scientific journal 
    Elusive in its free-base form, the core-modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p-tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy-substituted analogues (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). In the presence of trifluoroacetic acid (TFA), each of these compounds was transformed into the protonated thiatriphyrin(2.1.1), which exhibited moderate aromaticity. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Shoji, Taku, Yamamoto, Atsuyo, Shimomura, Erika, Maruyama, Mitsuhisa, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo, Morita, Noboru
    Chemistry Letters 42 (6) 638 - 640 0366-7022 2013 Scientific journal 
    The synthesis of 1,6′-biazulenes 3a and 3b and 1,6′:3,6″- terazulenes 7a and 7b was established by one-pot reactions via the Zincke-type ring-opening of the corresponding pyridinium salts with diethylamine, followed by the reaction with cyclopentadiene in the presence of sodium methoxide. The intramolecular charge-transfer characters between azulene rings were investigated by UVvis spectroscopy and theoretical calculations. © 2013 The Chemical Society of Japan.
  • John Mack, Jun Nakamura, Tetsuo Okujima, Hiroko Yamada, Hidemitsu Uno, Nagao Kobayashi
    Journal of Porphyrins and Phthalocyanines 17 (10) 996 - 1007 1099-1409 2013 Scientific journal 
    Magnetic circular dichroism (MCD) spectroscopy and TD-DFT calculations are used to analyze the electronic structure and optical properties of low-symmetry acenaphthoporphyrins with AAAB, ABAB and AABB structures. Evidence for dual fluorescence caused by tautomerism has been identified in the emission spectra of the AAAB and ABAB compounds. The sign sequences observed for the Q and B bands in the MCD spectra have been used to validate the results of the TD-DFT calculations. An anomalous +/- sign sequence is observed in the B band region with ascending energy similar to that reported previously for metal tetraphenyltetraacenaphthoporphyrin complexes. Copyright © 2013 World Scientific Publishing Company.
  • Shoji, Taku, Shimomura, Erika, Maruyama, Mitsuhisa, Maruyama, Akifumi, Ito, Shunji, Okujima, Tetsuo, Toyota, Kozo, Morita, Noboru
    European Journal of Organic Chemistry 2013 (34) 7785 - 7799 1434-193X 2013 Scientific journal 
    1-Ethynylazulenes connected by several arylamine cores reacted with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) in a formal [2+2] cycloaddition-cycloreversion reaction to afford the corresponding tetracyanobutadiene (TCBD) and dicyanoquinodimethane (DCNQ) chromophores, respectively, in excellent yields. The intramolecular charge-transfer (ICT) characters between the donor (azulene and arylamine cores) and acceptor (TCBD and DCNQ units) moieties were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the new TCBD and DCNQ derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions. 1-Ethynylazulenes connected by several types of arylamine cores reacted with TCNE and TCNQ in formal [2+2] cycloadditions to afford corresponding tetracyanobutadiene and dicyanoquinodimethane chromophores, respectively. Cyclic voltammetry of the chromophores revealed their multistep reduction properties; significant color changes were also visible during electrochemical reduction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Hiroko Yamada, Yuji Yamaguchi, Ryuta Katoh, Takao Motoyama, Tatsuya Aotake, Daiki Kuzuhara, Mitsuharu Suzuki, Tetsuo Okujima, Hidemitsu Uno, Naoki Aratani, Ken-ichi Nakayama
    CHEMICAL COMMUNICATIONS 49 (99) 11638 - 11640 1359-7345 2013 Scientific journal 
    P-n junction solar cells based on anthradithiophene (ADT) as a p-type semiconductor were fabricated by using the photoprecursor method in which an alpha-diketone-type precursor was spin-coated and then transformed to ADT in situ by photoirradiation. Combination with PC71BM as an n-layer material led to 1.54% photoconversion efficiency.
  • Hiroki Uoyama, Hiroko Yamada, Tetsuo Okujima, Hidemitsu Uno
    HETEROCYCLES 86 (1) 515 - 534 0385-5414 2012/12 Scientific journal 
    Ethanonaphthoporphyrins with a halogen atom at the zeta position were prepared by the [3+1] porphyrin synthesis of halogen-substituted ethanobenz[f]isoindole with a tripyrrane derivative. The halogeno porphyrins were converted to the corresponding ethynyl and pinacolatoboronyl compounds by Sonogashira and borylation reactions, respectively. Suzuki, Sonogashira, and Glaser coupling reactions of these ethanonaphthoporphyrins gave bis-porphyrins connected with no atom, acetylene, and butadiyne, respectively. Retro Diels-Alder reaction of these bis-porphyrins brought about the conversion of bicyclo[2.2.2]octadiene (BCOD) to benzene moieties to give bis-naphthoporphyrins, quantitatively.
  • Tetsuo Okujima, Akiko Toda, Yoko Miyashita, Ayumi Nonoshita, Hiroko Yamada, Noboru Ono, Hidemitsu Uno
    HETEROCYCLES 86 (1) 637 - 648 0385-5414 2012/12 Scientific journal 
    Bis(azulenylethynyl)thiophenes, terthiophenes, and dithienothiophenes have been synthesized by the Pd-catalyzed cross-coupling of the corresponding diiodothiophenes with 1- and 6-ethynylazulenes under Sonogashira-Hagihara conditions.
  • Taku Shoji, Shunji Ito, Tetsuo Okujima, Noboru Morita
    Organic & biomolecular chemistry 10 (41) 8308 - 13 1477-0520 2012/10 
    Azulene-substituted butadiynes have been prepared by Cu-mediated cross- and homo-coupling reactions. The azulene-substituted butadiynes reacted with tetracyanoethylene in a formal [2 + 2] cycloaddition reaction to afford the corresponding 1,1,4,4-tetracyanobutadiene chromophores, in excellent yields. Further [2 + 2] cycloaddition with TTF and TCNE gave novel donor-acceptor chromophores and novel azulene-substituted 6,6-dicyanofulvene derivatives.
  • Tetsuo Okujima, Tasuku Kikkawa, Haruyuki Nakano, Hiroshi Kubota, Nobumasa Fukugami, Noboru Ono, Hiroko Yamada, Hidemitsu Uno
    CHEMISTRY-A EUROPEAN JOURNAL 18 (40) 12854 - 12863 0947-6539 2012/10 Scientific journal 
    Bicyclo[2.2.2]octadiene (BCOD) fused azuliporphyrins were synthesized by 3+1 porphyrin synthesis of azulitripyrranes with diformylpyrroles. Subsequent retro-Diels-Alder reaction of the BCOD-fused azuliporphyrins afforded azulibenzo, azulidibenzo-, and azulitribenzoporphyrins 1-5. NMR and UV/Vis spectra, as well as nucleus-independent chemical shift (NICS) calculations revealed that 1-5 and their diprotonated dications exhibit relatively low porphyrinoid aromaticity, which was dependent on the position and number of fused benzene rings present.
  • Noboru Ono, Tetsuo Okujima
    Isocyanide Chemistry: Applications in Synthesis and Material Science 385 - 429 2012/08 In book
  • Quan Liu, Fan-Tai Kong, Tetsuo Okujima, Hiroko Yamada, Song-Yuan Dai, Hidemitsu Uno, Noboru Ono, Xiao-Zeng You, Zhen Shen
    TETRAHEDRON LETTERS 53 (26) 3264 - 3267 0040-4039 2012/06 Scientific journal 
    Bisdimethylfluorenylamino-based push-pull dyes bearing one or two benzo[c]thiophene and its precursor bicyclo[2.2.2]octadiene (BCOD) fused thiophene as it bridge have been synthesized. The effect of fused-ring on thiophene bridge for the spectroscopic and electrochemical properties of these dyes has been investigated. Dye-sensitized solar cells fabricated with these dyes show moderate photovoltaic properties. (C) 2012 Elsevier Ltd. All rights reserved.
  • Taku Shoji, Junya Higashi, Shunji Ito, Tetsuo Okujima, Masafumi Yasunami, Noboru Morita
    Organic & biomolecular chemistry 10 (12) 2431 - 8 1477-0520 2012/03 
    Arylethynyl-2H-cyclohepta[b]furan-2-ones reacted with 7,7,8,8-tetracyanoquinodimethane (TCNQ) in a formal [2 + 2] cycloaddition reaction, followed by ring opening of the initially formed cyclobutene derivatives, to afford the corresponding dicyanoquinodimethane (DCNQ) chromophores in excellent yields. The intramolecular charge-transfer (ICT) interactions between the 2H-cyclohepta[b]furan-2-one ring and DCNQ acceptor moiety were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the novel DCNQ derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties depended on the number of DCNQ units in the molecule. Moreover, a significant color change was observed by visible spectroscopy under electrochemical reduction conditions.
  • Tatsuya Aotake, Shinya Ikeda, Daiki Kuzuhara, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroko Yamada
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (9) 1723 - 1729 1434-193X 2012/03 Scientific journal 
    5,14-alpha-Diketopentacene, a structural isomer of 6,13-alpha-diketopentacene, was prepared from pentacene in three steps. In addition to the typical n-pi* absorption of the diketone moiety at around 468 nm and the anthracene-like absorption at 333, 349, and 367 nm, a broad absorption was observed at around 386 nm, which could be assigned to an intramolecular charge-transfer absorption from anthracene to the diketone moiety. 5,14-alpha-Diketopentacene could be converted into pentacene quantitatively by photoirradiation at 405 and 468 nm in toluene with quantum yields of 2.3 and 2.4%, respectively, and these values are higher than the quantum yield of 1.4% obtained for 6,13-alpha-diketopentacene irradiated at 468 nm. The quantum yields in acetonitrile were lowered to 0.33 and 0.28% with irradiation at 405 and 468 nm. The crystal structure of 5,14-alpha-diketopentacene showed a CH-pi interaction and pi-pi stacking between neighbouring anthracene and benzene moieties. The lower solubility of 5,14-alpha-diketopentacene compared with the 6,13-isomer could be explained by this crystal structure.
  • Takahiro Nakae, Ryuji Ohnishi, Yoshiharu Kitahata, Tatsuya Soukawa, Hisako Sato, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroshi Sakaguchi
    TETRAHEDRON LETTERS 53 (13) 1617 - 1619 0040-4039 2012/03 Scientific journal 
    6,13-Diiododibenzo[a,h]anthracene and 5,8-diiodopicene were synthesized by AuCl-catalyzed double cyclization. The highly selective reaction yielded a new class of pen-halogenated fused aromatics. (C) 2012 Elsevier Ltd. All rights reserved.
  • Shoji, Taku, Inoue, Yuta, Ito, Shunji, Okujima, Tetsuo, Morita, Noboru
    Heterocycles 85 (1) 35 - 41 0385-5414 2012 Scientific journal 
    An efficient synthesis of 2-heteroarylazulene derivatives was established via electrophilic substitution. The reaction of 6-dimethylamino-1,3- di(methylthio)azulene (1a) with the triflate of N-containing heteroarenes proceeded in the presence of excess heteroarenes to afford the corresponding 2-dihydroheteroarylazulene derivatives 3-7. The 2-dihydroheteroarylazulene derivatives were readily converted into the desired 2-heteroarylazulene derivatives 8-11 by the treatment with KOH in alcohols in excellent yields, except for 4 and 5. © 2012 The Japan Institute of Heterocyclic Chemistry.
  • Mitsunori Nakamura, Hiroyuki Tahara, Kohtaro Takahashi, Toshi Nagata, Hiroki Uoyama, Daiki Kuzuhara, Shigeki Mori, Tetsuo Okujima, Hiroko Yamada, Hidemitsu Uno
    ORGANIC & BIOMOLECULAR CHEMISTRY 10 (34) 6840 - 6849 1477-0520 2012 Scientific journal 
    Benzene-fused bis-(borondipyrromethene)s (bis-BODIPYs) were synthesized by retro-Diels-Alder reaction of the corresponding bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis-BODIPYs, which were, in turn, prepared from 4,8-ethano-4,8-dihydropyrrolo[3,4-f]isoindole derivatives. The pi-fused bis-BODIPY chromophores were designed to show intensive absorption and strong fluorescence in the near-infrared region and not to have any strong absorption in the visible region. A 6,10-dibora-5a,6a,9a,10a-tetraaza-s-indaceno[2,3-b:6,5-b']difluorene derivative (syn-bis-benzoBODIPY) obtained by a thermal retro-Diels-Alder reaction of the corresponding BCOD-fused BODIPY dimer has strong absorption and emission bands at 775 and 781 nm, respectively. The absolute quantum yield is 0.36. The absorption is more than 5.0 times stronger than other absorptions observed in the visible region. In the case of 6,15-dibora-5a,6a,14a,15a-tetraaza-s-indaceno[2,3-b:6,7-b']difluorene derivatives (anti-bis-benzoBODIPY), the absorption and emission maxima exceed 840 nm.
  • Hiroko Yamada, Chika Ohashi, Tatsuya Aotake, Shuhei Katsuta, Yoshihito Honsho, Hiroo Kawano, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono, Shu Seki, Ken-ichi Nakayama
    CHEMICAL COMMUNICATIONS 48 (90) 11136 - 11138 1359-7345 2012 Scientific journal 
    Hole mobility was evaluated by top-contact bottom gate field effect transistor and time resolved microwave conductivity measurements in 2,6-dithienylanthracene and hexyl-substituted 2,6-dithienylanthracene films prepared by spin-coating of their alpha-diketone precursors followed by photoirradiation, revealing enough high potentials for semiconducting films with charge carrier mobilities of 0.8-0.9 cm(2) V-1 s(-1) in the photo-irradiated films.
  • Hidemitsu Uno, Mina Furukawa, Akiko Fujimoto, Hiroki Uoyama, Hajime Watanabe, Tetsuo Okujima, Hiroko Yamada, Shigeki Mori, Makoto Kuramoto, Tatsunori Iwamura, Noriyuki Hatae, Fumito Tani, Naoki Komatsu
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 15 (9-10) 951 - 963 1088-4246 2011/09 Scientific journal 
    Facing zinc bisporphyrins connected with diethanoanthracene and diethanonaphthacene (syn-1 and syn-2) are prepared by double [3+1] porphyrin synthesis of tripyrranedicarbaldehyde with syn-5,11-dimethoxy-4,6,10,12-tetrahydro-4,12;6,10-diethanoanthracene[2,3-c;7,8-c']dipyrrole and syn-4,7,11,14-tetrahydro-4,14;7,11-diethanonaphthacene[2,3-c;8,9-c']dipyrrole. These bisporphyrins contain large clefts with different sizes capable for complexation with fullerenes such as C-60 and C-70. These designed syn-oriented bisporphyrins serve as effective and selective molecular tweezers for C-70. Binding affinity of the zinc bisporphyrins, namely, syn-1 and syn-2, towards C-60 and C-70 in solution is determined by employing UV-vis spectrophotometric technique. Values of binding constants (K) in toluene for the non-covalent complexes of syn-1 with C-60 and C-70 are estimated to be 3.1(4) x 10(4) and 5.0(2) x 10(5) M-1, respectively, and those of syn-2 with C-60 and C-70 are enumerated to be 2.1(4) x 10(4) and 1.70(13) x 10(5) M-1, respectively. Binding of C-60 and C-70 in the clefts of syn-1 and syn-2 is clearly demonstrated by the crystal structures of C-60/syn-1, C-70/syn-1, C-60/syn-2, and C-70/syn-2 complexes. In the crystal structures with C-70, the directions of the long axis of C-70 are found to be quite different: in the case of C-70/syn-1 complex the axis lies perpendicularly to the line connecting two zinc atoms; however, for the C-70/syn-2 complex, the axis occupies in-plane to the same line. Both the clefts of syn-1 and syn-2 are induced to fit the included fullerenes by domed out-of-plane distortion of porphyrin rings. Moreover, the bicyclo[2.2.2]octadiene moieties of syn-1 are widened by complexation with the fullerenes, while the same moieties of syn-2 are narrowed by the complexation. Therefore, syn-1 catches the fullerenes at the shallow part of the cleft. On the other hand, syn-2 catches the fullerenes at the bottom part of the cleft. NMR experiments of the complexes in THF-d(8) also support these orientations even in solution.
  • Daiki Kuzuhara, Hiroko Yamada, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 15 (9-10) 930 - 942 1088-4246 2011/09 Scientific journal 
    A series of benzoporphycenes and naphthoporphycenes and their zinc complexes were prepared from bicyclo[2.2.2]octadiene fused porphycenes by a retro-Diels-Alder reaction and their photophysical properties were studied. Free-base tetranaphthoporphycene was not soluble in common organic solvents, but zinc tetranaphthoporphycene was slightly soluble in pyridine and showed B- and Q-bands at 507 and 690 nm, respectively. Dinaphthoporphycene showed broad B- and Q-bands due to its lower symmetry. Tetrabenzo-, dibenzo-, and dinaphthoporphycenes showed fluorescence at 673, 654, and 670 nm with quantum yields of 0.32, 0.42, and 0.31, respectively, although their precursors were non-fluorescent. Zinc complexes of tetrabenzo-, dibenzo-, tetranaphtho-, dinaphthoporphycenes and their bicyclo[2.2.2]octadiene-fused precursors revealed moderate fluorescence with quantum yields of 0.15-0.37. The crystal structures of tetrabenzo-and dibenzoporphycenes showed herringbone structures, while the zinc tetrabenzoporphycene showed a hexagonal box-structure with six pyridine ligands inside.
  • Tetsuo Okujima, Guangnan Jin, Saika Otsubo, Shinji Aramaki, Noboru Ono, Hiroko Yamada, Hiroko Yamada, Hidemitsu Uno
    Journal of Porphyrins and Phthalocyanines 15 697 - 703 1088-4246 2011/07 
    Bicyclo[2.2.2]octadiene(BCOD)-fused diazaporphyrin was synthesized by the reaction of BCOD-fused dipyrromethane with sodium nitrite in acetic acid/ethanol in the presence of copper(II) acetylacetonate. This soluble precursor was converted into the semiconducting thin film of (tetrabenzodiazaporphyrinato) copper(II) by heating after fabrication via spin-coating. © 2011 World Scientific Publishing Company.
  • Hiroko Yamada, Daiki Kuzuhara, Shuhei Katsuta, Tetsuo Okujima, Hidemitsu Uno
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 69 (7) 802 - 813 0037-9980 2011/07 Scientific journal 
    This paper focuses on the synthesis of new aromatic compounds by thermal, photochemical, or oxidative cleavage reaction of the corresponding precursors. The precursor-methods are useful for the derivatization of the non-soluble aromatic compounds. We have applied retro Diels-Alder reactions for the preparation of new pi-expanded porphyrinoid compounds such as [14] tribenzo-triphyrin (2.1.1), tetrabenzoporphycene, dodecasubstituted porphycene, tetraanthraporphyin, butadiyne-linked tetrabenzoporphyrin dimer, and so on. We have investigated the photocleavage synthesis of pentacenes from the corresponding alpha-diketone precursors. This photoreaction enabled us to prepare 1,4,8,11-tetrasubstituted pentacene. The synthesis of new pentacene derivatives with electron-withdrawing substituents at 6,13-positions by oxidative cleavage reaction will be also reported.
  • Tetsuo Okujima, Guangnan Jin, Naoki Matsumoto, John MacK, Shigeki Mori, Keishi Ohara, Daiki Kuzuhara, Chie Ando, Noboru Ono, Hiroko Yamada, Hidemitsu Uno, Nagao Kobayashi
    Angewandte Chemie - International Edition 50 5699 - 5703 1433-7851 2011/06 
    Retro: Cyclo[8]isoindole, which has a saddle-shaped geometry (see picture, 2), was synthesized by oxidative coupling of a bicyclo[2.2.2]octadiene(BCOD)- fused 2,2′-bipyrrole followed by a retro-Diels-Alder reaction of BCOD-fused cyclo[8] pyrrole (1). Key trends in the optical spectra of ring-annelated cyclo[8]pyrroles are identified based on magnetic circular dichroism spectra and theorectical calculations. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Yuya Tornimori, Tetsuo Okujima, Tomoko Yano, Shigeki Mori, Noboru Ono, Hiroko Yamada, Hidemitsu Uno
    TETRAHEDRON 67 (18) 3187 - 3193 0040-4020 2011/05 Scientific journal 
    A pi-expanded BODIPY dye with an intramolecular boronate skeleton was synthesized by retro Diets-Alder reaction of the bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY and the subsequent O-chelation. The photophysical and electrochemical properties were examined by UV-vis, fluorescence, CV measurements, and DFT calculation. This BODIPY exhibited the absorption and emission over a visible-NIR region at 600-850 nm. O-chelated BODIPY showed a bathocromic shift compared to F-BODIPYs. This dye showed a bright fluorescence emission at 733 nm with the high phi value of 0.58. (C) 2011 Elsevier Ltd. All rights reserved.
  • Taku Shoji, Junya Higashi, Shunji Ito, Tetsuo Okujima, Masafumi Yasunami, Noboru Morita
    Chemistry (Weinheim an der Bergstrasse, Germany) 17 (18) 5116 - 29 0947-6539 2011/04 
    Ethynylated 2H-cyclohepta[b]furan-2-ones 5-15 have been prepared by Pd-catalyzed alkynylation of 3-iodo-5-isopropyl-2H-cyclohepta[b]furan-2-one (2) with the corresponding ethynylarenes or the reaction of 2-iodothiophene with 3-ethynyl-5-isopropyl-2H-cyclohepta[b]furan-2-one (4) under Sonogashira-Hagihara conditions. Compounds 5-15 reacted with tetracyanoethylene in a formal [2+2] cycloaddition reaction, followed by ring opening of the initially formed [2+2] cycloadducts, cyclobutenes, to afford the corresponding 1,1,4,4-tetracyanobutadienyl (TCBD) chromophores 16-26 in excellent yields. The intramolecular charge-transfer interactions between the 2H-cyclohepta[b]furan-2-one ring and TCBD acceptor moiety were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the novel TCBD derivatives 16-26 was examined by cyclic voltammetry and differential pulse voltammetry, which revealed multistep electrochemical reduction properties, depending on the number of TCBD units in the molecule. Moreover, a significant color change was observed by UV/Vis spectroscopy under electrochemical reduction conditions.
  • Pyosang Kim, Jooyoung Sung, Hiroki Uoyama, Tetsuo Okujima, Hidemitsu Uno, Dongho Kim
    JOURNAL OF PHYSICAL CHEMISTRY B 115 (14) 3784 - 3792 1520-6106 2011/04 Scientific journal 
    We have investigated the role of fused benzo rings on the electronic structures and intramolecular energy relaxation dynamics in a series of benzoporphyrins (Bpl, syn-Bp2, anti-Bp2, Bp3, and Bp4) by using time-resolved fluorescence measurements and theoretical calculations. Interestingly, even though anti- and syn-Bp2 have the same number of fused anti-Bp2 benzo rings, in the respective absorption spectra, shows an obvious splitting of B(x) (Q(x)) and B(y) (Q(y)) states, whereas syn-Bp2 exhibits degenerate B and Q bands. These features provide two dynamical models for the effect of the position of substituted benzo rings on the intramolecular energy relaxation dynamics. syn-Bp2 gives rise to similar intrarnolecular dynamics from the B state to the Q state in the case of ZnTPP having Do molecular symmetry. On the other hand, anti-Bp2 shows split B and Q bands in the order B(y) > B(x) > Q(x) > Q(y), which leads a superimposition of the Q(x) (0,0) and Q(y) (1,0) bands. This overlap generates a strong coupling between these two states, which results in a direct internal conversion from B(x) (0,0) to Q(y) (0,0). This observation suggests that the anti-type fused position of benzo rings leads to a new mechanism in internal conversion from the B to the Q state. On the basis of this work, further insight was obtained into the effect of fused benzo rings on the photophysical properties of benzoporphyrins, providing a detailed understanding of the structure-property relationship in a series of benzoporphyrins.
  • Daiki Kuzuhara, Hiroko Yamada, Keiko Yano, Tetsuo Okujima, Shigeki Mori, Hidemitsu Uno
    CHEMISTRY-A EUROPEAN JOURNAL 17 (12) 3376 - 3383 0947-6539 2011/03 Scientific journal 
    The synthesis of dodecasubstituted porphycenes has not been reported, to date. Herein, the preparation of tetramethyloctaethylporphycene by a McMurry-type coupling of 3,3', 4,4'-tetraethyl-5,5'-diformyl-2,2'-bipyrrole was attempted at first, but dodecasubstituted porphycene was not successfully obtained and only pyrrolocyclophene was obtained. The structure of the pyrrolocyclophene was determined by H-1 NMR spectroscopy, FAB MS, and X-ray crystal-structure analysis. The pyrrolocyclophene was not successfully oxidized to porphycene. Then, the McMurry-type coupling of bicyclo[2.2.2]octadiene (BCOD)-fused 5,5'diacyl-2,2'-bipyrroles was performed and tetra-meso-octa-beta-substituted (dodecasubstituted) porphycenes were successfully obtained for the first time. The structures were determined by H-1 NMR spectroscopy and X-ray crystal-structure analysis. The crystal structures and NMR spectra were compared carefully with octasubstituted porphycenes, and there was a good correlation between the position of the substituents, the N1-N2 and N1-N4 distances of the porphycene inner nitrogen atoms, and NMR chemical shifts of the inner NH protons, which expressed the strength of N-H center dot center dot center dot N hydrogen bonding between N1 and N2. These results suggested that the BCOD structure was relatively compact compared with common alkyl groups and that was why the dodecasubstituted porphycenes were available this time. UV/Vis absorption and fluorescence properties are also discussed.
  • Shuhei Katsuta, Daichi Miyagi, Hiroko Yamada, Tetsuo Okujima, Shigeki Mori, Ken-ichi Nakayama, Hidemitsu Uno
    ORGANIC LETTERS 13 (6) 1454 - 1457 1523-7060 2011/03 Scientific journal 
    5,12-Dicyanonaphthacene and 6,13-dicyanopentacene have been synthesized for the first time. The LUMO and HOMO levels are deepened as predicted and fabricated organic field-effect transistors (OFETs) showed ambipolar responses with carrier mobilities of 10(-3) cm(2)/V.s.
  • Shoji, Taku, Higashi, Junya, Ito, Shunji, Okujima, Tetsuo, Morita, Noboru
    European Journal of Organic Chemistry (3) 584 - 592 1434-193X 2011 Scientific journal 
    Novel bis(3-methylthio-1-azulenyl)methyl cations 3a + and 3b + and dications 4a 2+ and 4b 2+ were synthesized by thehydride abstraction reaction of the corresponding hydride derivatives 7a, 7b, 8a, and 8b, which were readily prepared by the acid-catalyzed condensation reaction of 6a and 6b with the corresponding aldehyde and dialdehyde with DDQ. The pK R + values of novel cations 3a + and 3b + and dications 4a 2+ and 4b 2+ were determined spectrophotometrically to examine the thermodynamic stability of these carbocations. The redox behavior of the mono- and dications was also examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their reversible electrochemical reduction properties, except for the case of dication 4b 2+ . Moreover, a significant color change was observed by visible spectroscopy under electrochemical reduction conditions. Dications 4a 2+ and 4b 2+ were also chemically reduced by Zn powder to afford thienoquinoid compounds 9a and 9b, respectively. Bis(3-methylthio-1-azulenyl)methyl cations and dications were synthesized from the corresponding hydride derivatives, which were prepared by the acid-catalyzed condensation reaction of 1-methylthioazulenes with aldehydes and dialdehydes with DDQ. These novel carbocations exhibited reversible electrochemical reduction properties. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Daiki Kuzuhara, Hiroko Yamada, ZhaoLi Xue, Tetsuo Okujima, Shigeki Mori, Zhen Shen, Hidemitsu Uno
    CHEMICAL COMMUNICATIONS 47 (2) 722 - 724 1359-7345 2011 Scientific journal 
    The metal-free and meso-free [14]triphyrin(2.1.1) compound was successfully prepared based on the intramolecular McMurry coupling reaction of diformyl-tripyrrane in 16% yield, and was converted to the bowl-shaped Mn(I)(TriP)(CO)(3) and Re(I)(TriP)(CO)(3).
  • Shoji, Taku, Ito, Shunji, Okujima, Tetsuo, Morita, Noboru
    European Journal of Organic Chemistry (26) 5134 - 5140 1434-193X 2011 Scientific journal 
    The ene-diyne systems 1 and 2, possessing ferrocenyl groups at the periphery, were prepared by a simple one-pot Sonogashira-Hagihara coupling reaction of ethynylferrocene with 9-dibromomethylene-9H-fluorene (4) and 9,10-bis(dibromomethylene)-9,10-dihydroanthracene (5). Ene-diyne 1 reacted with tetracyanoethylene (TCNE) in a formal [2+2] cycloaddition reaction, followed by ring opening of the initially formed [2+2] cycloadduct, cyclobutene, to afford the corresponding 1,1,4,4-tetracyanobutadiene (TCBD) derivative 6 in good yield. The redox behavior of the ene-diyne compounds 1 and 2, and the TCBD derivative 6 was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their electrochemical oxidation properties with multi-electron transfer depending on the number of ferrocene units in the molecule, in addition to the two-electron reduction of the TCBD moiety in the case of TCBD derivative 6. Moreover, a significant color change was observed by visible spectroscopy under electrochemical oxidation conditions and under reduction conditions in the case of TCBD derivative 6. Ene-diyne systems with ferrocenyl groups at the periphery were prepared by theSonogashira-Hagihara reaction and reacted with tetracyanoethylene in a [2+2] cycloaddition reaction to afford the 1,1,4,4-tetracyanobutadiene derivative in goodyield. The redox behavior was examined by cyclic voltammetry and differential pulse voltammetry; significant color changes were observed. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Shuhei Katsuta, Kazuki Tanaka, Yukihiro Maruya, Shigeki Mori, Sadahiro Masuo, Tetsuo Okujima, Hidemitsu Uno, Ken-ichi Nakayama, Hiroko Yamada
    CHEMICAL COMMUNICATIONS 47 (36) 10112 - 10114 1359-7345 2011 Scientific journal 
    Novel bisimide-fused acenes were synthesized via bismuth triflate mediated double-cyclization reaction of acid chlorides and isocyanates. Their optical and electrical properties revealed significantly smaller HOMO-LUMO gaps compared with those of their parent acenes. Fabricated OFET based on tetracene bisimide showed n-type OFET outputs.
  • Hiroko Yamada, Kei Ohkubo, Daiki Kuzuhara, Tetsuro Takahashi, Atula S. D. Sandanayaka, Tetsuo Okujima, Keishi Ohara, Osamu Ito, Hidemitsu Uno, Noboru Ono, Shunichi Fukuzumi
    JOURNAL OF PHYSICAL CHEMISTRY B 114 (45) 14717 - 14728 1520-6106 2010/11 Scientific journal 
    Free base and zinc porphyrins are linked with fullerene (C(60)) through beta,beta`-pyrrolic positions rather than meso-positions by Diels-Alder reaction of monoanthraporphyrins (H(2)P-mA and ZnP-mA) and C(60) to afford a pi-expanded free base porphyrin-fullerene dyad (H(2)P-C(60)) and its zinc porphyrin-fullerene dyad (ZnP-C(60)) in 86 and 51% yield, respectively The X-ray crystallographic analysis of ZnP-C(60) showed two comma-shaped swirls-like structure in a unit cell The intramolecular center-to-center and edge-to-edge distances between the porphyrin and fullerene moieties were 11 5 and 2 5 angstrom, respectively The porphyrins and fullerenes were packed in layer-by-layer structure and the porphyrins lied down in parallel The Intermolecular center-to-center distances between the neighboring fullerenes were 10 252, 10028, and 10 129 angstrom, which were less than typical van der Waals distance and the pi-pi interaction spread two-dimensionally The energy of the charge-separated (CS) state of ZnP-C(60) (1 11 eV) determined by differential-pulse voltammetry measurements in benzonitrile is significantly lower than those of zinc porphyrin-C(60) dyads linked at meso positions because of the low oxidation potential of the a-expanded ZnP moiety The CS energy of ZnP-C(60) in a nonpolar solvent such as toluene (1 40 V) is lower than the triplet excited state of C(60) ((3)C(60)*), enabling us to attain a longed lived triplet CS state (8 1 mu s) in toluene, detected by nanosecond laser flash photolysis experiments The distance between unpaired electrons in the triplet CS state was determined by the EPR spectrum to be 9 1 angstrom, which agreed with the distance between a zinc atom of the porphyrin and a carbon edge of C(60) in the crystal structure of ZnP-C(60) The rate constants of photoinduced electron transfer and back electron transfer of H(2)P-C(60) and ZnP-C(60), which were determined by femtosecond and nanosecond laser flash photolysis measurements, were analyzed in light of the Marcus theory of electron transfer
  • Tetsuo Okujima, Yuya Tomimori, Jun Nakamura, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    TETRAHEDRON 66 (34) 6895 - 6900 0040-4020 2010/08 Scientific journal 
    A series of pi-expanded boron-dipyrromethenes (BODIPYs) fused with aromatic rings at beta,beta-positions, such as benzene, acenaphthylene, and benzofluoranthene were prepared by the reaction of BF(3)center dot OEt(2) with bicyclo[2.2.2]octadiene-fused dipyrromethene and the subsequent retro Diels-Alder reaction. These BODIPYs exhibited the absorptions and the fluorescence emissions over wide range of visible-near infrared region at 500-800 nm. BODIPYs composed of two fluorantho[8,9-f]isoindoles absorbed and emitted at red-region over 750 nm with absolute fluorescence quantum yield (Phi(f)) of ca. 0.3, although they are unstable under air in room light. BODIPY composed fluorantho[8,9-f]isoindole and acenaphtho [1,2-c]pyrrole was stable and showed a bright fluorescence emission at 695 nm with high Phi(f) of 0.70. (C) 2010 Elsevier Ltd. All rights reserved.
  • Hiroki Uoyama, Hiroko Yamada, Tetsuo Okujima, Hidemitsu Uno
    TETRAHEDRON 66 (34) 6889 - 6894 0040-4020 2010/08 Scientific journal 
    15-Acetoxy- and 15-hydroxy-6,13-dihydro-6,13-ethanopentacenes sublimed over 300 degrees C and no pentacene was formed below the temperature. The precursors bearing chlorinated epithiomethano bridges suffered complicated decomposition to give oligomeric pentacene derivatives. The precursor bearing an epithio-oxomethano bridge underwent smooth and clean conversion to pentacene by heat or light. An organic field-effect transistor fabricated by the spin-coating method of the precursor followed by light irradiation at 120 degrees C showed a good FET performance of mu=2.5 x 10(-2) cm(2) V-1 s(-1) and on/off ratio=3.8 x 10(4). (C) 2010 Elsevier Ltd. All rights reserved.
  • Tetsuo Okujima, Tasuku Kikkawa, Saori Kawakami, Yusuke Shimizu, Hiroko Yamada, Noboru Ono, Hidemitsu Uno
    TETRAHEDRON 66 (35) 7213 - 7218 0040-4020 2010/08 Scientific journal 
    Bicyclo[2.2.2]octadiene(BCOD)-fused trithiasapphyrin was prepared by 3+2 condensation of BCOD-fused thiatripyrrane with BCOD-fused bithiophene. The BCOD-fused trithiasapphyrin was successfully converted to pentabenzo[b,g,l,q,v]sapphyrin by the thermal retro-Diels-Alder reaction. In this case, trithiapentabenzo[b,g,l,q,v]- and trithiadibenzo[g,q]sapphyrins were selectively prepared by control of the temperature in the thermal retro-Diels-Alder reaction. (C) 2010 Elsevier Ltd. All rights reserved.
  • Hiroki Uoyama, Cai Chenxin, Hiroyuki Tahara, Yusuke Shimizu, Hideki Hagiwara, Yasuaki Hanasaki, Hiroko Yamada, Tetsuo Okujima, Hidemitsu Uno
    HETEROCYCLES 80 (2) 1187 - 1196 0385-5414 2010/03 Scientific journal 
    4,11-Ethano-4,11-dihydro-2H-anthra[2,3-c]pyrrole and 4,11-ethano-4,11-dihydroanthra[2,3-c]thiophene derivatives were prepared from the corresponding bicyclo[2.2.2]octadiene-fused five-membered heterocycles by the Diels-Alder reaction with in situ generated alpha, alpha'-dibromo-o-xylylene derivatives. Their thermogravimetric analyses showed evapolation without formation of 2H-anthra[2,3-c]pyrrole and anthra[2,3-c]thiophene derivatives under the atmospheric pressure.
  • Jun Nakamura, Tetsuo Okujima, Yuya Tomimori, Naoki Komobuchi, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    HETEROCYCLES 80 (2) 1165 - 1175 0385-5414 2010/03 Scientific journal 
    Tetrabenzoporphyrins fused with fluoranthenes were prepared by the retro Diels-Alder reaction of the precursors composed of a porphyrin and four fluoranthenes connected with bicyclo[2.2.2]octadiene (BCOD). These porphyrins exhibited the Soret (480-494 nm, epsilon = 243,000-277,000) and intense Q bands (739-760 nm, epsilon = 375,000-509,000). Free bases and Zn complexes of them fluoresce at 760 nm and 746 nm with small Storks shifts and high quantum yields of 30 and 10 %, respectively.
  • Shuhei Katsuta, Hiroko Yamada, Tetsuo Okujima, Hidemitsu Uno
    TETRAHEDRON LETTERS 51 (10) 1397 - 1400 0040-4039 2010/03 Scientific journal 
    The syntheses of 1,4,8,11-tetraphenylpentacene and 1,4,8,11-tetra(2'-thienyl)pentacene are described via photodecarbonylation of the corresponding alpha-diketone precursors. (C) 2010 Elsevier Ltd. All rights reserved.
  • Hiroki Uoyama, Kil Suk Kim, Kenji Kuroki, Jae-Yoon Shin, Toshi Nagata, Tetsuo Okujima, Hiroko Yamada, Noboru Ono, Dongho Kim, Hidemitsu Uno
    CHEMISTRY-A EUROPEAN JOURNAL 16 (13) 4063 - 4074 0947-6539 2010 Scientific journal 
    Tetrameric porphyrin formation of 2-hydroxymethylpyrrole fused with porphyrins through a bicyclo[2.2.2]octadiene unit gave bicyclo[2.2.2]octadiene-fused porphyrin pentamers. Thermal conversion of the pentamers gave fully pi-conjugated cruciform porphyrin pentamers fused with benzene units in quantitative yields. UV/Vis spectra of fully pi-conjugated porphyrin pentamers showed one very strong Q absorption and were quite different from those of usual porphyrins. From TD-DFT calculations, the HOMO level is 0.49 eV higher than the HOMO-1 level. The LUMO and LUMO + 1 levels are very close and are lower by more than 0.27 eV than those of other unoccupied MOs. The strong Q absorption was interpreted as two mutually orthogonal single-electron transitions (683 nm: 86%, HOMO -> LUMO; 680 nm: 86%, HOMO -> LUMO + 1). The two-photon absorption (TPA) cross section value (sigma((2))) of the benzene-fused porphyrin pentamer was estimated to be 3900 GM at 1500 nm, which is strongly correlated with a cruciform molecular structure with multidirectional pi-conjugation pathways.
  • Hiroko Yamada, Daiki Kuzuhara, Kei Ohkubo, Tetsuro Takahashi, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono, Shunichi Fukuzumi
    JOURNAL OF MATERIALS CHEMISTRY 20 (15) 3011 - 3024 0959-9428 2010 Scientific journal 
    A new alpha-diketoporphyrin and the corresponding Pd complex were prepared from the monoanthroporphyins and their photochemical properties were investigated by measurements of absorption and emission spectra, fluorescence lifetimes, laser flash photolysis, cyclic voltammetry, and theoretical calculations. Intramolecular electron transfer from the porphyrin singlet excited state to the diketone moiety was observed for the free base alpha-diketoporphyrin in benzonitrile, but this was not observed in toluene. Photoreactivity of the alpha-diketoporphyrins was also examined by irradiation at the Soret and Q bands. When the Soret band of the freebase alpha-diketoporphyrin was irradiated, cleavage of the diketone moiety occurred to afford the monoanthroporphyrin with the release of two CO molecules quantitatively in both benzonitrile and toluene. When the Q band of the freebase alpha-diketoporphyrin was irradiated, no photocleavage reaction occurred in toluene. In contrast to the freebase alpha-diketoporphyrin, the photocleavage reaction of the Pd complex occurred with irradiation at the Q band as well as the Soret band to afford the monoanthroporphyrin quantitatively in toluene. The photocleavage reaction proceeded much more effectively in toluene than in benzonitrile. The occurrence of rapid photoinduced electron transfer from the singlet excited state porphyrin to the diketone moiety, which was detected by femtosecond laser flash photolysis measurements, results in a significant decrease in the singlet excited state lifetime, prohibiting the photocleavage reaction in benzonitrile. Thus, the Pd alpha-diketoporphyrin can act as an excellent precursor for the corresponding acene in toluene. The photocleavage process provides a convenient and inexpensive method to make the thin film.
  • Guangnan Jin, Tetsuo Okujima, Yusuke Hashimoto, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS 185 (5-6) 1108 - 1116 1042-6507 2010 Scientific journal 
    This article describes the preparation of (ethylenedithio)bicyclo[2.2.2]octadiene-fused porphyrins 13 and 14a,b as soluble precursors of 2,3-dihydrobenzo[1,4]dithiin-fused porphyrins and the retro Diels-Alder conversion of the precursors 13 and 14a,b.
  • Shunji Ito, Takahiro Iida, Jun Kawakami, Tetsuo Okujima, Noboru Morita
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (31) 5355 - 5364 1434-193X 2009/11 Scientific journal 
    Enediyne scaffolds connected by a 9,10-anthracenediyl spacer as a redox-active substructure with 6-azulenyl groups as pi-electron-accepting groups in their periphery (3a and 3b) have been prepared by a one-pot reaction involving repeated Pd-catalyzed alkynylation of 6-haloazulenes 7b and 7c with bis(enediyne) derivative 6. The azulene-substituted bis(enediyne)s 3a and 3b exhibited two reversible one-step, two-electron reduction proper-ties upon cyclic voltammetry (CV) attributable to the formation of dianionic and tetraanionic species. The electrochemical reduction of 3a and 3b led a strong absorption in the near-IR region corresponding to the formation of the stabilized dianionic species 3a(RED)(2-) and 3b(RED)(2-). An electrochromic analysis revealed the lower stability of the tetraanionic species 3a(RED)(4-..) and 3b(RED)(4-..), although the CV exhibited good reversibility. The mono(enediyne) systems 11a and 11b were also prepared for comparison. The electrochemical reduction of 11a and 11b did not exhibit good electrochemical reversibility by CV, but the electrochemical reduction led to a strong absorption in the near-IR region, similar to the formation of the stabilized dianionic species 3a(RED)(2-) and 3b(RED)(2-) in the bis(enediyne) systems. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
  • Tetsuo Okujima, Akihiro Mifuji, Jun Nakamura, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    ORGANIC LETTERS 11 (18) 4088 - 4091 1523-7060 2009/09 Scientific journal 
    Synthesis of [Ru(phenP)(3)](PF(6))(2), where phenP = phenanthrolinoporphyrin, has been achieved by the reaction of phenanthrolinoporphyrins with RuCl(3) for the first time. The phenP reacted with Ru(II) to form RuL(2)(phenP)(2+) complexes (L = 2,2'-bipyridine or 1,10-phenanthroline), which were converted Into the dyads Ru-phenP(Zn) on treatment with zinc acetate.
  • Akane Masumoto, Yuko Yamashita, Shintetsu Go, Toshihiro Kikuchi, Hiroko Yamada, Tetsuo Okujima, Noboru Ono, Hidemitsu Uno
    JAPANESE JOURNAL OF APPLIED PHYSICS 48 (5) 0515051 - 0515055 0021-4922 2009/05 Scientific journal 
    Organic thin-film transistors were successfully fabricated by the spin-coating method using a photo-precursor of pentacene, 6,13-dihydro-6,13-ethanopentacene-15,16-dione. After spin coating the soluble precursor, irradiation with visible light gave a pentacene film. A good mobility of 0.34 cm(2) V(-1) s(-1) and a high on/off ratio of 2.0 x 10(6) were achieved by treatment of the insulator surface with methyl silsesquioxane and by deposition of pentacene from the precursor with visible light irradiation (>300 nm) and mild heat treatment (110-120 degrees C). In this case, small grains of pentacene crystals existed in the loosely ordered pentacene mesophase, in which pentacene molecules aligned vertically. Not only the grains of pentacene crystals but also the loosely packed pentacene phase played an important role in the field-effect transistor (FET) performance. (C) 2009 The Japan Society of Applied Physics
  • Taiji Akiyama, Hiroki Uoyama, Tetsuo Okujima, Hiroko Yamada, Noboru Ono, Hidemitsu Uno
    TETRAHEDRON 65 (22) 4345 - 4350 0040-4020 2009/05 Scientific journal 
    Nitration of 4,7-ethanoisoindoles gave 1-nitro derivatives in moderate yields. Reduction of a nitro to amino group was successfully performed by sodium hydrosulfite in the case of ethyl 3-nitro-4,7-ethanoisoindole-1-carboxylate. The amino derivative was converted to benzylidenaminoisoindoles based on the retro Diels-Alder reaction. Their UV-vis spectra showed strong absorptions at 500-700 nm. (C) 2009 Elsevier Ltd. All rights reserved.
  • Taku Shoji, Shunji Ito, Tetsuo Okujima, Junya Higashi, Ryuji Yokoyama, Kozo Toyota, Masafumi Yasunami, Noboru Morita
    European Journal of Organic Chemistry 1554 - 1563 1434-193X 2009/04 
    Electrophilic ipso-substitution reactions between 1,3,6-tritert- butylazulcne (2) and several electrophilic reagents were examined. Friedel-Crafts and Vilsmeier reactions of 2 gave the corresponding ipso-substitution products in moderate to excellent yields. One of the ipso-substitution products, 1,6- di-tert-butyl-3-formylazulene (5), was converted in high yield into the synthetically more useful azulene derivative 1,6-di-tert-butylazulene (1) by decarbonylation on treatment with pyrrole in acetic acid. Treatment of 2 with N-[(trifluoromelhyl)su]fonyl] pyridinium trifluoromethanesulfonate (TPT) unexpectedly afforded 1- trifluoromethylthioazulene 10 and l(8H)-azulenone 11. Compound 2 also reacted with tetracyanoethylene (TCNE) to give an excellent yield of cycloaddition product 13, rather than the ipso-substitution reaction product. © Wiley-VCH Verlag GmbH & Co. KGaA.
  • Tetsuo Okujima, Yusuke Hashimoto, Guangnan Jin, Hiroko Yamada, Noboru Ono
    HETEROCYCLES 77 (2) 1235 - 1248 0385-5414 2009/02 Scientific journal 
    Soluble precursors of beta-, meso-unsubstituted mono-, di- and tribenzoporphyrins were prepared by the reaction of dimethylbicyclo[2.2.2]octadiene-fused pyrrole with appropriate beta-free pyrroles. The retro Diels-Alder reaction of these precursors afforded the corresponding benzoporphyrins in quantitative yields.
  • Daiki Kuzuhara, John Mack, Hiroko Yamada, Tetsuo Okujima, Noboru Ono, Nagao Kobayashi
    CHEMISTRY-A EUROPEAN JOURNAL 15 (39) 10060 - 10069 0947-6539 2009 Scientific journal 
    The first facile syntheses of free-base di- and tetrabenzoporphycenes and their metal complexes; are reported. based on retro-Diels-Alder reactions of the corresponding bicyclo(2.2.2]octadiene-fused porphycenes. prepared by McMurray coupling of alpha,alpha'-diformyldipyrrole. The photophysical and electrochemical properties are analyzed based on UV/Vis absorption. magnetic circular dichroism (MCD). and fluorescence emission. lifetime and quantum yield measurements, cyclic and differential pulse voltammetry (CV and DPV) and time-dependent DFT calculations based on B3LYP geometry optimizations. Benzoporphycenes are found to be prime candidates for future use in photodynamic therapy.
  • Jun Nakamura, Noboru Ono, Hiroko Yamada, Tetsuo Okujima
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS 505 349 - 355 1542-1406 2009 Scientific journal 
    Acenaphtho[1,2-b]porphyrins (AcePs) were prepared by the [3 + 1] condensation method and their photochemical properties were investigated. The fluorescence spectra of the free-base AcePs in CHCl(3) showed two emission bands at 660 and 720 nm, whose intensity drastically changed depending on the excitation wavelength. However, those of zinc complexes did not show such a wavelength dependence and showed similar emission spectra by the excitation at various wavelengths. The fluorescence excitation spectra and quantum yields of the free-base AcePs in CHCl(3) showed the similar excitation wavelength dependence. This fact indicates that two electronic structures exist in the free-base AcePs and their fluorescence is emitted from one structure in higher quantum yield (lambda(EM) = 660 nm) and from the other in lower yield (lambda(EM) = 720 nm), respectively.
  • Zhao-Li Xue, Zhen Shen, John Mack, Daiki Kuzuhara, Hiroko Yamada, Tetsuo Okujima, Noboru Ono, Xiao-Zeng You, Nagao Kobayashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130 (49) 16478 - + 0002-7863 2008/12 Scientific journal 
    The synthesis and spectroscopic properties of a series of boron-free meso-aryl-substituted [14]triphyrin(2.1.1) compounds containing either peripheral bicyclo[2.2.2]octadiene (BCOD) (2a-c) or benzene rings (3a-c) (aryl = phenyl. a, 4-fluorophenyl b, and 4-methylbenzoatephenyl c) are reported. These compounds represent the first examples of free-base contracted porphyrinoids with 14 TT-electron aromatic systems containing only the standard pyrrole and isoindoline moieties of the porphyrins and tetrabenzoporphyrins.
  • Hiroko Yamada, Kayo Kushibe, Satoshi Mitsuogi, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono
    TETRAHEDRON LETTERS 49 (32) 4731 - 4733 0040-4039 2008/08 Scientific journal 
    One of 5-alkenyl-15-alkynyl-porphyrin and 5,15-dialkynyl-porphyrin was prepared selectively by 2+2 acid-catalyzed condensation of bicyclo[2.2.2]octadiene-fused dipyrrylmethane and TMS propynal in the presence of BF(3) OEt(2) only by the choice of the solvent. The alkenyl group was expected to be obtained by a protonation followed by intramolecular 1,2-hydride transfer from methine position of porphyrinogen. (C) 2008 Elsevier Ltd. All rights reserved.
  • Hiroko Yamada, Daiki Kuzuhara, Tetsuro Takahashi, Yusuke Shimizu, Keisuke Uota, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono
    ORGANIC LETTERS 10 (14) 2947 - 2950 1523-7060 2008/07 Scientific journal 
    Linearly pi-expanded novel tetraanthroporphyrins with and without aromatic rings at the meso-positions were prepared quantitatively for the first time from the corresponding precursors by a retro-Diels-Alder reaction.
  • Shunji Ito, Tetsuo Okujima, Shigeru Kikuchi, Taku Shoji, Noboru Morita, Toyonobu Asao, Tadaaki Ikoma, Shozo Tero-Kubota, Jun Kawakami, Akio Tajiri
    The Journal of organic chemistry 73 (6) 2256 - 63 0022-3263 2008/03 
    Several azulene-substituted thioketones, 1-thiobenzoylazulene (1a) and di(1-azulenyl) thioketone (2a) and their derivatives (1b and 2b-d) with alkyl substituents on each azulene ring, were prepared and their intramolecular pericyclization reaction was examined. The thioketones with a 3-alkyl substituent on each azulene ring exhibited the presumed pericyclization reaction under thermal and acid-catalyzed conditions, although the cases of the 1-azulenyl thioketones without the 3-alkyl substituents afforded a complex mixture under similar conditions. The intramolecular reaction following the intramolecular hydrogen transfer afforded the products 13b, 14b, and 14c. The products 13b and 14b were converted into the corresponding cations 18(+) and 19(+), which have structural similarity with that of the phenalenyl cation. These cations exhibited the expected two-step reduction waves upon CV, although the ESR analysis revealed that the neutral radical state did not have the presumed high stability.
  • Tetsuo Okujima, Yusuke Hashimoto, Guangnan Jin, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    TETRAHEDRON 64 (10) 2405 - 2411 0040-4020 2008/03 Scientific journal 
    This paper describes the preparation of dimethylbicyclo[2.2.2]octadiene-fused porphyrins as extremely soluble precursors of tetrabenzoporphyrins and thermal conversion of the precursors to tetrabenzoporphyrins. (C) 2008 Elsevier Ltd. All rights reserved.
  • Hidernitsu Uno, Yusuke Shimizu, Hiroki Uoyama, Yousuke Tanaka, Tetsuo Okujima, Noboru Ono
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (1) 87 - 98 1434-193X 2008/01 Scientific journal 
    Multistep thermal fragmentation of quadruply bicyclo[2.2.2]octadiene-fused porphyrins giving tetrabenzoporphyrins was examined in detail. After the first extrusion of an ethylene molecule from the porphyrin derivative, the opposite bicyclo[2.2.2]octadiene moiety preferentially underwent the second retro-Diels-Alder reaction to give an opp-dibenzoporphyrin derivative rather than an adj-dibenzoporphyrin derivative. These two benzoporphyrin derivatives then decomposed to give a tribenzoporphyrin derivative in similar rates. The temperature regions of these fragmentations could not be distinguished by thermogravimetric analysis. In contrast, the third and the fourth fragmentations obviously occurred stepwise. There was a temperature region where the tribenzoporphyrin derivative preferentially existed. In the case of the 21,23-dithiaporphyrin derivative, opp-21,23-dithiadibenzoporphyrin, possessing benzo moieties fused at the pyrrole parts of the core-modified porphyrin chromophore was predominantly formed during the fragmentation. In the case of the 21-thiaporphyrin derivative, an ethylene molecule was extruded selectively from the bicyclo[2.2.2]octadiene moiety adjacent to the thiophene part to give 21-thiabenzo[q]phyrin and then 21-thiabenzo[g,q]porphyrin derivatives. In these cases, the last ethylene extrusion also occurred very slowly. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
  • John Mack, Masaru Bunya, Yusuke Shimizu, Hiroki Uoyama, Naoki Komobuchi, Tetsuo Okujima, Hidemitsu Uno, Satoshi Ito, Martin J. Stillman, Noboru Ono, Nagao Kobayashi
    CHEMISTRY-A EUROPEAN JOURNAL 14 (16) 5001 - 5020 0947-6539 2008 Scientific journal 
    The optical spectra of a series of core-modified tetrabenzoporphyrins were analyzed to determine the effects of core modification, ligand folding, and partial benzo substitution at the ligand periphery on the electronic structure by using magnetic circular dichroism (MCD) and NMR spectroscopy, X-ray crystallography, cyclic and differential pulse voltammetry, and TD-DFT calculations. Planar 21-carba-, 21-thia-, 21,23-dithia-, and 21-oxa-23thiatetrabenzo[b,g,l,q]porphyrins reported previously were studied together with the previously unreported 21-oxa- and 21-carba-23-thiatetrabenzo[b,g,l,q]porphyrins. The optical properties of these compounds are compared to those of tetrabenzo[b,g,l,q]-, 5,.10,15,20-tetraphenyl-, 5,10,15,20-tetraphenyltetrabenzo[b,g,l,q]-21-thia-, 5,10,15,20-tetraphenyltetrabenzodithia-, 5,10,15,20-tetraphenyldibenzo[g,q]21,23-dithia-, 5,10,15,20-tetraphenyldibenzo[b,t]-21,23-ditliia-, 5,10,15,20tetraphenyltribenzo[g,q]-1-21-thia-, and 5,10,15,20-tetraphenylbenzo[b]-21-thia- porphyrins. Michl's perimeter model and Gouterman's four-orbital model are used to conceptualize the results and to account for red shifts commonly observed in the spectral bands of nonplanar porphyrinoids.
  • Hiroko Yamada, Tetsuo Okujimaa, Noboru Ono
    CHEMICAL COMMUNICATIONS (26) 2957 - 2974 1359-7345 2008 
    Solution processable organic semiconducting small molecules are desirable for the manufacture of low-cost, large-area electronic products on flexible substrates. This article provides an overview of recent progress in OFETs based on solution processable small molecules that can be converted to insoluble organic semiconducting materials on films by thermal or photochemical removal of leaving groups after fabrication of the film.
  • Atsuko Hirao, Taiji Akiyama, Tetsuo Okujima, Hiroko Yamada, Hidemitsu Uno, Yoshimasa Sakai, Shinji Aramaki, Noboru Ono
    CHEMICAL COMMUNICATIONS (39) 4714 - 4716 1359-7345 2008 Scientific journal 
    Soluble precursors of 2,3-naphthalocyanine (Nc) and phthalocyanine (Pc) were prepared and were converted into insoluble semiconducting thin films of Pc and Nc by heating after fabrication via spin-coating.
  • Yan-Hong Yu, Zhen Shen, Hai-Yun Xu, Yan-Wei Wang, Tetsuo Okujima, Noboru Ono, Yi-Zhi Li, Xiao-Zeng You
    JOURNAL OF MOLECULAR STRUCTURE 827 (1-3) 130 - 136 0022-2860 2007/02 Scientific journal 
    Two new 8-(4-dimethylaminophenyl) substituted boron-dipyrromethene (BDP) dyes: 1,2,6,7-tetraethyl-4,4-difluoro-3,5-dimethyl8-(4-dimethylaminophenyl)-4-bora-3a,4a-diaza-s-indacene (5) and 4,4-difluoro-1,2,3,5,6,7-hexamethyl-8-(4-dimethylaminophenyl)4-bora-3a,4a-diaza-s-indacene (6) have been synthesized and their crystal structures are determined by X-ray diffraction analysis. The torsion angles of 8-phenyl ring and the indacene plane are 79.61 degrees for 5 and 87.56 degrees for 6, respectively. The absorption and steady-state fluorescence properties in different solvents have been investigated. The fluorescence quantum yields of the two dyes are lower in more polar solvents, which can be ascribed to the intramolecular charge transfer from the aniline to the BDP unit. Protonation of the aniline moiety at low pH in MeOH-H2O (1:1 v/v) solution causes a large fluorescence enhancement. The pk(a) values calculated from the pH dependent fluorescence emission spectra are 3.14 for 5 and 3.09 for 6, respectively. They are suitable as pH probes excitable with visible light. (c) 2006 Elsevier B.V. All rights reserved.
  • Hiroko Yamada, Naoko Kamio, Akihiro Ohishi, Manami Kawano, Tetsuo Okujima, Noboru Ono
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 11 (5-6) 383 - 389 1088-4246 2007 Scientific journal 
    Tetrabenzoporphyrin films on indium-tin-oxide electrodes were prepared by continuous spin-coating of indium-tin-oxide electrodes with a soluble precursor, tetrabicyclo[2.2.2]octadiene-fused porphyrin, and subsequent thermal conversion of the precursor to tetrabenzoporphyrin by annealing the modified electrodes. When the tetrabenzoporhyrin-modifled indium-tin-oxide working electrode was irradiated in a three-electrode system, using Pt as a counter electrode and Ag/Ag+ as a reference electrode in the presence of hexyl viologen as an electron acceptor, a cathodic photocurrent was observed. A double layer structure consisting of tetrabenzoporphyrin and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) films and a triple layer structure consisting of tetrabenzoporphyrin; a mixture of tetrabenzoporphyrin and PCBM; and PCBM films were also prepared on indium-tin-oxide electrodes by repeated spin coating. The incident photon to photocurrent efficiency values of up to 6.8% were obtained for the triple layer structure, in which the mixed layer contained tetrabenzoporphyrin and PCBM molecules in. a, 7:3 ratio. Action-spectra of the-triple layer structure showed that visible light from 380 to 700 nm sensitized the system for photocurrent generation. Copyright (C) 2007 Society of Porphyrins & Phthalocyanines.
  • Taiji Akiyama, Atsuko Hirao, Tetsuo Okujima, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    HETEROCYCLES 74 835 - 842 0385-5414 2007 Scientific journal 
    Mg complex of phthalocyanine fused with bicyclo[2.2.2]octadiene (BCOD) units is prepared by the reaction of BCOD-fused phthalonitrile with Mg(OPr)(2) in PrOH at 100 degrees C overnight in 42% yield. Subsequent heating the product at 250 degrees C results in clean formation naphthalocyanine via the retro Diels-Alder reaction. An attempt to the synthesis of BCOD-fused tetraazaporphyrin by the similar cyclization of the Diels-Alder adduct of dicyanoacetylene with 1,3-cyclohexadiene was unsuccessful.
  • Tetsuo Okujima, Guangnan Ji, Yusuke Hashimoto, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    Heterocycles 70 619 - 626 0385-5414 2006/12 
    Diels-Alder reaction of ethynyl p-tolyl sulfone with 1,3-dienes gave the corresponding tosyl-1,4-cyclohexadienes. The resulting adducts could be converted into 4,7-dihydro-2H-isoindole derivatives including bicyclo[2.2.2]ocatadiene(BCOD)-fused pyrrole as an isoindole equivalent. © 2006 The Japan Institute of Heterocyclic Chemistry.
  • Hiroko Yamada, Emi Kawamura, Sadaaki Sakamoto, Yuko Yamashita, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono
    TETRAHEDRON LETTERS 47 (42) 7501 - 7504 0040-4039 2006/10 Scientific journal 
    A diketone precursor of air-stable bis-2-thienyl-2,6-anthracene was prepared and quantitatively converted to the target acene by photoirradiation of the n-pi* absorption both in solution and as a film, in air. (c) 2006 Elsevier Ltd. All rights reserved.
  • HY Xu, Z Shen, T Okujima, N Ono
    CHINESE JOURNAL OF INORGANIC CHEMISTRY 22 (5) 801 - 807 1001-4861 2006/05 Scientific journal 
    Two new exocyclic ring-fused boron-dipyrromethene (BDP) dyes with benzo crown ether subunit at meso-position were prepared. Their spectroscopic and electrochemical properties were investigated. The introduction of the electron withdrawing ester groups to the chromophore makes compound 2 to be a very sensitive fluorescent probe for Na+ analysis.
  • HJ Xu, Z Shen, T Okujima, N Ono, XZ You
    TETRAHEDRON LETTERS 47 (6) 931 - 934 0040-4039 2006/02 Scientific journal 
    A series of meso-tetraaryl porphyrins with fused phenanthrene rings have been synthesized from boron trifluoride-catalyzed Lindsey condensation of phenanthro[9, 10-c]pyrrole with various para-substituted arylaldehydes at low temperature. Their structures were characterized by UV-vis, H-1 NMR, and mass spectroscopies. The UV-vis spectra of these compounds showed remarkable bathochromic shift of the Soret band to the wavelength around 577 nm and Q-bands into the near-infrared region. (c) 2005 Elsevier Ltd. All rights reserved.
  • T Okujima, N Komobuchi, H Uno, N Ono
    HETEROCYCLES 67 (1) 255 - 267 0385-5414 2006/01 Scientific journal 
    Benzoporphyrins fused with acenaphthylene or fluoranthene (3) and (4) were prepared by the condensation of bicyclo[2.2.2]octadiene(BCOD)-fused tripyrrane (5) with appropriate pyrrole dialdehydes (13) or (14) and the subsequent retro Diels-Alder reaction. The absorptions of these new porphyrins were very intense at both Soret and Q bands, which might be useful as organic dyes for solar cells.
  • H Yamada, K Kushibe, T Okujima, H Uno, N Ono
    CHEMICAL COMMUNICATIONS (4) 383 - 385 1359-7345 2006/01 Scientific journal 
    5-Alkenyl-15-alkynylporphyrins have been obtained unexpectedly by [2 + 2] acid-catalyzed condensation of dipyrrylmethane and TMS propynal in addition to 5,15-dialkynylporphyrin, and the unsymmetrical porphyrin can be converted to a butadiyne-linked dimer by selective desilylation of the alkynyl TMS.
  • Tetsuo Okujima, Makoto Kikuchi, Hiroko Yamada, Hidemitsu Uno, Noboru Ono
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 10 (9-10) 1197 - 1201 1088-4246 2006 Scientific journal 
    Soluble tetra(pyrazino)tetraazaporphyrin was synthesized by the reaction of bicyclo[2.2.2]octadiene-fused dicyanopyrazine. The retro Diels-Alder reaction of the soluble tetra(pyrazino)tetraazaporphyrin gave a tetra(quinoxalino)tetraazaporphyrin in quantitative yield. Copyright (c) 2006 Society of Porphyrins & Phthalocyanines.
  • H Yamada, Y Yamashita, M Kikuchi, H Watanabe, T Okujima, H Uno, T Ogawa, K Ohara, N Ono
    CHEMISTRY-A EUROPEAN JOURNAL 11 (21) 6212 - 6220 0947-6539 2005/10 Scientific journal 
    A novel alpha-diketone precursor of pentacene, 6,13-dihydro-6,13-ethanopentacene-15,16-dione, was prepared and converted successfully to pentacene in 74% yield by photolysis of the precursor in toluene: Irradiation of the diketone solution in toluene with light of 460 nm under an Ar atmosphere caused the solution to change from yellow to fluorescent orange-pink within a few minutes, after which, purple precipitates appeared. After 35 min, the solution changed to colorless and the purple precipitates were filtered to give pentacene in 74% yield. By contrast, in the presence of oxygen, the color of the solution changed from yellow to pale yellow., and only 6,13-endoperoxide of pentacene was quantitatively obtained. The rate of the reaction upon photolysis was measured by observing the decay of n-pi* absorption of the precursor at 460 nm, and was found to be similar in both the presence and absence of oxygen. Therefore, the photoreaction of the alpha-diketone precursor seemed to occur via the singlet excited state. Because the T-T absorption of pentacene was observed upon photolysis of the precursor in the nanosecond transient absorption measurement under an Ar atmosphere, the excited triplet state of the pentacene generated singlet oxygen by sensitization, and it reacted with the ground-state pentacene to give the 6,13-endoperoxide. The alpha-diketone deposited on glass was also converted successfully to pentacene film by photoirradiation. In addition, diketone precursors of a mixture of 2,8- and 2,9-di-bromopentacene and 2,6-trianthrylene were also prepared and their photoconversion was performed.
  • H Uno, Y Yamashita, M Kikuchi, H Watanabe, H Yamada, T Okujima, T Ogawa, N Ono
    TETRAHEDRON LETTERS 46 (12) 1981 - 1983 0040-4039 2005/03 Scientific journal 
    6,13-Dihydro-6,1 3-ethanopentacene-15,16-dione gave pentacene efficiently both in solid and in solution by irradiation of light. (C) 2005 Elsevier Ltd. All rights reserved.
  • T Okujima, N Komobuchi, Y Shimizu, H Uno, N Ono
    TETRAHEDRON LETTERS 45 (28) 5461 - 5464 0040-4039 2004/07 Scientific journal 
    A bicyclo[2.2.2]octadiene-fused tripyrrane was synthesized as a first versatile reagent for the preparation of pi-expanded heteroporphyrins. The reaction of the tripyrrane with 1,3-diformylindene and azulene-1,3-dicarbaldehyde afforded the corresponding heteroporphyrins. which were easily converted into tetrabenzocarbaporphyrin and tribenzoazuliporphyrin by retro Diels-Alder reaction. (C) 2004 Elsevier Ltd. All rights reserved.
  • S Ito, T Terazono, T Kubo, T Okujima, N Morita, T Murafuji, Y Sugihara, K Fujimori, J Kawakami, A Tajiri
    TETRAHEDRON 60 (25) 5357 - 5366 0040-4020 2004/06 Scientific journal 
    This paper describes an efficient preparation of 2-azulenylboronate (6) starting from 2-iodoazulene by halogen-metal exchange reaction using n-BuLi and subsequent quenching with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The boronate 6 has been found to undergo Pd-catalyzed Miyaura-Suzuki cross-coupling reaction with a range of aryl bromides including aromatic poly bromides utilizing Pd-2(dba)(3)-P(t-Bu)(3) as a catalyst and establishes a strategy to produce novel poly(2-azulenyl)benzenes, some of which are found to be insoluble in common organic solvents, however. The redox behavior of 2-arylazulenes and poly(2-azulenyl)benzenes was examined by cyclic voltammetry (CV) and compared with those of 6-azulenylbenzene derivatives reported previously. (C) 2004 Elsevier Ltd. All rights reserved.
  • Y Shimizu, Z Shen, T Okujima, H Uno, N Ono
    CHEMICAL COMMUNICATIONS 10 (4) 374 - 375 1359-7345 2004/02 Scientific journal 
    Successful synthesis of a series of highly conjugated porphyrin analogues, including thia-, dithia- and oxathia-tetrabenzoporphyrins, and their optical properties are reported.
  • R Yokoyama, S Ito, T Okujima, T Kubo, M Yasunami, A Tajiri, N Morita
    TETRAHEDRON 59 (41) 8191 - 8198 0040-4020 2003/10 Scientific journal 
    Amination of 2-substituted azulene was carefully examined using several types of amines, and the scope and limitation of substrates and reagents in these direct nucleophilic aminations were found. The synthesis of 2-aminoazulenes was successfully achieved by the reaction of 2-bromoazulene with several amines via palladium-catalyzed amination. (C) 2003 Elsevier Ltd. All rights reserved.
  • S Ito, T Okujima, C Kabuto, N Morita
    TETRAHEDRON 59 (25) 4651 - 4659 0040-4020 2003/06 [Peer-reviewed]
     Scientific journal 
    Preparation and cycloaddition reaction of novel azulene-substituted N-sulfinylamines I and 2 are reported. The influence of the -N=S=O group on the UV-vis and NMR spectra of the azulene ring to which it is bonded is discussed. X-ray crystal analysis of 1 revealed the syn-configuration and the twisted structure of the N-sulfinylamine moiety. The synthetic utility of I and 2 have been explored by the cycloaddition reaction to afford novel azulene-substituted heterocycles under high-pressure conditions. We also described herein the synthesis and some proper-ties of related 2-azulenylisothiocyanate. (C) 2003 Elsevier Science Ltd. All rights reserved.
  • S Ito, R Yokoyama, T Okujima, T Terazono, T Kubo, A Tajiri, M Watanabe, N Morita
    ORGANIC & BIOMOLECULAR CHEMISTRY 1 (11) 1947 - 1952 1477-0520 2003/05 Scientific journal 
    2-Azulenyl trifluoromethanesulfonate was prepared by the reaction of 2-hydroxyazulene with trifluoromethanesulfonic anhydride in the presence of triethylamine as a base. Under the use of pyridine, 1-trifluoromethane-sulfonylpyridinium trifluoromethanesulfonate further reacted with 2-azulenyl trifluoromethanesulfonate to give 1-(1-trifluoromethanesulfonyl-1,4-dihydropyridin-4-yl) azulenyl trifluoromethanesulfonate. Moreover, we found that azulenes also reacted with 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate to give 4-(1-azulenyl)1,4- dihydropyridine derivatives and 6-(1-azulenyl)-1-trifluoromethanesulfonyl-1-aza-hexa-1,3,5-triene depending on the reaction conditions. 2-Azulenyl trifluoromethanesulfonate was converted finally into the parent azulene in excellent yield by palladium-catalyzed reduction using formic acid as a reducing reagent.
  • SJ Ito, T Okujima, N Morita
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (16) 1896 - 1905 1472-7781 2002/08 [Peer-reviewed]
     Scientific journal 
    The first versatile organometallic reagents derived from azulenes, i.e.. 6-(tri-n-butylstannyl)azulene (1a) and its, 1,3-diethoxycarbonyl derivative (1b), have been prepared by Pd(o)-catalyzed direct stannylation of 6-bromoazulenes, with bis(tri-n-butyltin). We demonstrate the utility of the reagents in the Stille cross-coupling reaction with aryl.acetyl and azulenyl halides to afford 6-aryl-, 6-acyl- and bi-azulenes in good yield. Furthermore. the methodology was applied to the synthesis of poly(azulen-6-yl)benzene derivatives. The reaction of 1b with 1.4-di-, 1,3,5-tri-. 1,2,4,5-tetra- and hexabromobenzenes afforded 1.4-di-, 1,3,5-tri-, 1,2,4,5-tetra-, 1,2,4-tri- and 1,2,3,5-tetra(azulen-6-yl)benzene derivatives (18, 20, 22, 24 and 25). The redox behavior of 18 and 22 was examined by cyclic voltammetry (CV) and compared with those of 20 and 24 reported previously. In contrast to the three-step reduction of 20, the compound 18 exhibited a reversible one-step two-electron reduction wave at - 1.30 V Upon CV, which revealed the formation of a closed-shell dianion. The four azulen-6-yl substituents on benzene in a 1,2,4,5 relationship increased electron-accepting properties because of the formation of a closed-shell dianion stabilized by four azulen-6-yl groups. As expected, the compound 22 exhibited a color change during the electrochemical reduction. However, the reverse oxidation did not regenerate the spectrum of 22 due to the low stability of the presumed dianionic species under the conditions of the UV-vis measurement.
  • T Okujima, S Ito, N Morita
    TETRAHEDRON LETTERS 43 (7) 1261 - 1264 0040-4039 2002/02 [Peer-reviewed]
     Scientific journal 
    The first versatile organometallic reagents of azulenes, 6-(tri-n-butylstannyl)azulenes, have been prepared by a Pd(0)-catalyzed direct stannylation of 6-bromoazulenes with bis(tri-n-butyltin). We demonstrate herein the utility of the reagents in the Stille cross-coupling reaction with aryl and azulenyl halides to afford 6-aryl- and biazulenes in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • S Ito, S Kikuchi, T Okujima, N Morita, T Asao
    JOURNAL OF ORGANIC CHEMISTRY 66 (7) 2470 - 2479 0022-3263 2001/04 [Peer-reviewed]
     Scientific journal 
    The titled stable monocations, di(1-azulenyl)(2- and 3-thienyl)methyl cations 7a,b and 8a,b and dications composed of two di( 1-azulenyl)methylium units connected with 2,5-thiophenediyl and 2,5-thieno[3,2-b]thiophenediyl spacers 9a,b and 10a,b were prepared by hydride abstraction of the corresponding methane derivatives. These mono- and dications 7a,b, 8a,b, 9a,b, and 10a,b showed high stability with large pK(R)(+) values. The values of monocations 7a,b and 8a,b were 11.2-11.8 +/- 0.1 and 11.4-12.4 +/- 0.1, respectively. Two cation units in dications 9a,b and 10a,b were neutralized via one step at the pH of 11.1-11.7 +/- 0.1, which corresponds to the average of the pK(R)(+) values of the dications and half-neutralized monocations. Electrochemical behavior of 7a,b, 8a,b, ga,b, and 10a,b was examined by cyclic voltammetry (CV). Formation of the thienoquinoid products 18a,b and 19a,b from 9a,b and 10a,b was characterized by UV-vis spectroscopy under electrochemical reduction conditions. Chemical reduction of 9a,b and 10a,b with Zn powder in acetonitrile afforded 18a,b and 19a,b as deep-colored crystals, which exhibited rather high electron-donating ability.
  • T Okujima, T Terazono, S Ito, N Morita, T Asao
    HETEROCYCLES 54 (2) 667 - + 0385-5414 2001/02 [Peer-reviewed]
     Scientific journal 
    Diazuleno[2,1-b:1,2-e]pyridines (2a and 2b) were prepared in one pot by the reaction of 2-aminoazulene (1a) with paraformaldehyde or benzaldehyde in moderate yields. Bis(2-amino-3-ethoxycarbonyl-1-azulenyl)methane (8a) was formed by the reaction of ethyl 2-aminoazulene-1-carboxylate (1b) with 1/2 molar amount of paraformaldehyde. Treatment of 8a with paraformaldehyde at room temperature afforded three heterocyclic compounds (9, 10, and 11). When 2-acetylaminoazulenes (1c and 1d) were used for this reaction, bis(2-acetylamino-1-azuleny)methanes (8b and 8c) were exclusively formed.
  • S Ito, H Inabe, T Okujima, N Morita, M Watanabe, N Harada, K Imafuku
    TETRAHEDRON LETTERS 42 (6) 1085 - 1089 0040-4039 2001/02 [Peer-reviewed]
     Scientific journal 
    Described herein is a cobalt-mediated cyclooligomerization of mono- and di(6-azulenyl)acetylenes to afford 1,3,5- and 1,2,4-tri(b-azulenyl)benzene derivatives and (eta (5)-cyclopentadienyl)[tetra- and di(6-azulenyl)cyclobutadiene]cobalt complexes. The redox behavior of these novel tri(6-azulenyl)benzene derivatives and [tetra- and di(6-azulenyl)cyclobutadiene]cobalt complexes examined by cyclic voltammetry is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • S Ito, H Inabe, T Okujima, N Morita, M Watanabe, K Imafuku
    TETRAHEDRON LETTERS 41 (43) 8343 - 8347 0040-4039 2000/10 [Peer-reviewed]
     Scientific journal 
    1,2-Di(6-azulenyl)tetraphenylbenzenes and (6-azulenyl)pentaphenylbenzenes were synthesized by Diels-Alder reaction of di(6-azulenyl)acetylenes and 6-(phenylethynyl)azulenes with tetraphenylcyclopentadienone. Mono(6-azulenyl)benzenes exhibited a reduction wave upon cyclic voltammetry (CV). In contrast to the benzene derivatives, di(6-azulenyl)benzenes showed a two-step reduction wave at similar potential region upon CV, which revealed the formation of dianions stabilized by 6-azulenyl substituents under electrochemical reduction conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
  • M Oda, T Kajioka, T Okujima, S Itoh, N Morita, R Miyatake, S Kuroda
    CHEMISTRY LETTERS (10) 1011 - 1012 0366-7022 1997 [Peer-reviewed]
     Scientific journal 
    The title carbocation, generated from 1,1-ethylene-1,6-dihydroazulene and trityl tetrafluoroborate in deuterated acetonitrile at - 20 degrees C, was characterized by means of lcw temperature NMR spectroscopy, and was found to undergo expansion of the cyclopropane ring at elevated temperature and to react with nucleophiles to give the addition products at the cyclopropane methylene carbon.

Books etc

  • Near-Infrared Dyes Based on Ring-Expanded Porphyrins with No Meso-Bridges
    OKUJIMA Tetsuo (Contributor, Light-Active Functional Organic Materials, 2019, Chap 6, 115-131.)
    Pan Stanford Publishing Pte. Ltd. (Eds. Yamada, Hiroko; Yagai, Shiki) 2019/03
  • Charging Up the Future by Organic Solar Cells
    OKUJIMA Tetsuo (Contributor, Functional Materials: Advances and Applications in Energy Storage and Conversion, 2019, 419-465)
    Pan Stanford Publishing Pte. Ltd. (Ed. Naito Toshio) Singapore 2019/01
  • 高共役拡張ポルフィリノイドの合成
    奥島鉄雄, 宇野英満 (Joint work, J. Synth. Org. Chem. 2018, 76, 690-698.(有機合成化学協会誌))
    2018
  • Synthesis of rigid  organic molecular architectures and applications for a single molecular measurement
    Uno, Hidemitsu, Nakae, Takahiro, Okujima, Tetsuo, Mori, Shigeki (Joint work, Molecular Archtectonics: The Third Stage of Single Molecule Electronics)
    Springer 2017
  • Synthesis of a Porphyrin-Fused π-Electron System
    Uno, Hidemitsu, Tagawa, Kazunari, Watanabe, Hajime, Kawamoto, Naoki, Furukawa, Mina, Okujima, Tetsuo, Mori, Shigeki (Joint work, Chemical Science of π-Electron System, 2015, Part I (Extension of Planar pi-Electron Systems), Chap 2, 17-36.)
    Springer 2015
  • Synthesis of Pyrroles and Their Derivatives from Isocyanides
    Ono, Noboru, Okujima, Tetsuo (Joint work, Isocyanide Chemistry, Application in Synthesis and Materials Science 2012, 385-429.)
    Wiley-VCH 2012
  • Synthesis of Porphyrins Fused with Aromatic Rings
    Ono, Noboru, Yamada, Hiroko, Okujima, Tetsuo (Joint work, Handbook of Porphyrin Science 2010, 2, 1-102.)
    World Scientific 2010
  • Supramolecules Based on Porphyrins
    Yamada, Hiroko, Okujima, Tetsuo, Ono, Noboru (Joint work, Topics in Heterocyclic Chemistry 2008, 17 (Heterocyclic Supramolecules I), 123-159.)
    Springer 2008

Conference Activities & Talks

  • Selective synthesis of cyclo[n]pyrroles  [Not invited]
    Tetsuo Okujima, Hiroki Matsumoto, Chie Ando, Shigeki Mori, Masayoshi Takase, Hidemitsu Uno, Nagao Kobayashi
    第49回複素環化学討論会  2020/09
  • ジアザポルフィリンとアザコロールの合成  [Not invited]
    上田友貴, 井上真奈美, 森 重樹, 髙瀬雅祥, 内藤俊雄, 宇野英満, 奥島鉄雄
    第46回有機典型元素化学討論会
  • 可溶性フタロシアニン前駆体の合成と有機薄膜太陽電池の作製  [Not invited]
    古南滋登, 村松航太, 金藤大地, 森 重樹, 髙瀬雅祥, 宇野英満, 山田容子, 奥島鉄雄
    第46回有機典型元素化学討論会
  • 非対称なヘテロール三量体を前駆体としたシクロ[n]ピロールの合成  [Not invited]
    白石竜海, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2019ハロゲン利用ミニシンポジウム(第12回臭素化学懇話会年会in新潟)  2019/11
  • ペリレンイミド縮環ピロールの合成  [Not invited]
    鈴木結衣, 松本宏樹, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2019ハロゲン利用ミニシンポジウム(第12回臭素化学懇話会年会in新潟)  2019/11
  • ピロール・アズレン縮環アザコロネンの構造-物性相関の解明  [Not invited]
    佐々木良城, 髙瀬雅祥, 奥島鉄雄, 森 重樹, 宇野英満
    第30回基礎有機化学討論会  2019/09
  • ターピロールを前駆体としたシクロ[n]ピロールの選択的合成  [Not invited]
    松本宏樹, 森 重樹, 髙瀬雅祥, 宇野英満, 小林長夫, 奥島鉄雄
    第30回基礎有機化学討論会  2019/09
  • ピロール縮環アザコロネン二量体の合成  [Not invited]
    藤川佳乃, 佐々木良城, 髙瀬雅祥, 森 重樹, 奥島鉄雄, 宇野英満
    第35回若手化学者のための化学道場in島根  2019/09
  • 新規π拡張BODIPYの合成  [Not invited]
    中野英之, 村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第35回若手化学者のための化学道場in島根  2019/09
  • 環拡張ポルフィリン合成の新展開  [Invited]
    奥島 鉄雄
    第35回若手化学者のための化学道場in島根  2019/09
  • A New Approach for the Synthesis of Phenathroporphyrin  [Not invited]
    OKUJIMA Tetsuo
    18th International Symposium on Novel Aromatic Compounds (ISNA-18)  2019/07
  • Synthesis of the Soluble Precursors of Tetrabenzoporphyrin: Control of the Solubility and the Conversion Temperature  [Not invited]
    OKUJIMA Tetsuo
    18th International Symposium on Novel Aromatic Compounds (ISNA-18)  2019/07
  • テトラベンゾポルフィリン可溶性前駆体の合成と塗布型OFETの開発  [Not invited]
    奥島 鉄雄
    リサーチユニット研究会:機能性固体材料の最前線  2019/03
  • シクロ[9]ピロールの環サイズ選択的合成と物性  [Not invited]
    松本宏樹, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    日本化学会第99春季年会  2019/03
  • Near-Infrared Dyes Based on Ring-Expanded Porphyrins with No Meso-Bridges  [Invited]
    OKUJIMA Tetsuo
    10th Singapore International Chemistry Conference (SICC10)  2018/12
  • 核置換ヘキサフィリン(1.0.0.1.0.0)の合成と芳香族性  [Not invited]
    奥島鉄雄, 稲葉勇人, 小積遼平, 森 重樹, 髙瀬雅祥, 小林長夫, 宇野英満
    第12回有機π電子系シンポジウム  2018/11
  • ターピロールを原料としたシクロ[9]ピロールの合成  [Not invited]
    松本宏樹, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2018年日本化学会中国四国支部大会  2018/11
  • ジアザポルフィリンとアザコロールの合成  [Not invited]
    上田友貴, 井上真奈美, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2018/11
  • 核置換シクロ[n]ピロールの合成  [Not invited]
    白石竜海, 小積遼平, 髙瀬雅祥, 森 重樹, 宇野英満, 奥島鉄雄
    2018年日本化学会中国四国支部大会  2018/11
  • イソインドール前駆体を利用した新規フェナントレノポルフィリンの合成と物性  [Not invited]
    村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2018年日本化学会中国四国支部大会  2018/11
  • 核置換シクロ[n]ピロールの合成  [Not invited]
    白石竜海, 小積遼平, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第34回若手化学者のための化学道場(in高知)  2018/09
  • 新規meso縮環フェナントレノポルフィリンの合成  [Not invited]
    村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第29回基礎有機化学討論会  2018/09
  • 含アズレン環拡張/環縮小ポルフィリンの合成  [Not invited]
    稲葉勇人, 小積遼平, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第29回基礎有機化学討論会  2018/09
  • Selective Synthesis of Ring-expanded Porphyrins with No Meso-bridges  [Invited]
    OKUJIMA Tetsuo
    有機合成化学協会中国四国支部第78回パネル討論会  2018/07
  • Synthesis of Planar [34]Octaphyrin(1.0.1.0.1.0.1.0) and Core-Modified [24]Hexaphyrin(1.0.0.1.0.0)  [Invited]
    OKUJIMA Tetsuo
    Tenth International Conference on Porphyrins and Phthalocyanines (ICPP-10)  2018/07
  • 核置換シクロ[n]ピロールの合成  [Not invited]
    白石竜海, 小積遼平, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第113回有機合成シンポジウム  2018/06
  • 核置換アメチリン類の合成と物性  [Not invited]
    稲葉勇人, 小積遼平, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第113回有機合成シンポジウム  2018/06
  • Synthesis of Tetrabenzoporphyrin Complexes Bearing Peripheral Phenyl Groups  [Invited]
    OKUJIMA Tetsuo
    233rd ECS Meeting  2018/05
  • 1,5-ジアザフルバレンの合成と物性  [Not invited]
    奥島鉄雄, 松﨑悠也, 志田陽一, 森 重樹, 中江隆博, 髙瀬雅祥, 宇野英満
    日本化学会第98春季年会  2018/03
  • アズレンを組み込んだ環拡張ポルフィリンの合成  [Not invited]
    稲葉勇人, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第8回分子アーキテクトニクス研究会  2017/12
  • 含硫黄環拡張ポルフィリンの合成と物性  [Not invited]
    OKUJIMA Tetsuo
    第44回有機典型元素化学討論会  2017/12
  • 新規テトラフェナントレノポルフィリンの合成を指向した置換基を有するBCOD縮環ピロールの合成  [Not invited]
    村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2017ハロゲン利用ミニシンポジウム(第10回臭素化学懇話会年会in松山)  2017/11
  • 核置換シクロ[12]ピロールの合成  [Not invited]
    白石竜海, 石渡美沙樹, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2017ハロゲン利用ミニシンポジウム(第10回臭素化学懇話会年会in松山)  2017/11
  • ジアザポルフィリン銅錯体の合成  [Not invited]
    上田友貴, 井上真奈美, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2017ハロゲン利用ミニシンポジウム(第10回臭素化学懇話会年会in松山)  2017/11
  • 前駆体法を用いた塗布型有機薄膜太陽電池材料の合成  [Invited]
    奥島 鉄雄
    2017年日本化学会中国四国支部大会  2017/11
  • π共役拡張型ビス(ピロリルメチレン)ヒドラジン-ホウ素錯体の合成  [Not invited]
    松﨑悠也, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第28回基礎有機化学討論会  2017/09
  • Scholl反応を鍵とした新規テトラフェナントレノポルフィリンの合成  [Not invited]
    村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第28回基礎有機化学討論会  2017/09
  • 前駆体法を用いたベンゾポルフィリンの化学修飾  [Not invited]
    村松航太, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第111回有機合成シンポジウム  2017/06
  • アセナフチレン縮環π拡張型BOPHYの合成と物性  [Not invited]
    松﨑悠也, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    日本化学会第97春季年会  2017/03
  • 塗布型有機薄膜太陽電池の実現に向けた有機材料の開発  [Invited]
    奥島 鉄雄
    第2回有機エレクトロニクス研究会(2016年度)  2017/01
  • ジアザフルバレン骨格を有する新規電子受容性分子の合成  [Not invited]
    松﨑悠也, 志田陽一, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第43回有機典型元素化学討論会  2016/12
  • 次世代型太陽電池の実現に向けた有機材料の開発  [Invited]
    奥島 鉄雄
    第64回中国四国産学連携科学フォーラム  2016/11
  • syn-ジアザフルバレン類縁体の合成  [Not invited]
    稲葉勇人, 松﨑悠也, 日浦暢大, 志田陽一, 髙瀬雅祥, 森 重樹, 宇野英満, 奥島鉄雄
    2016ハロゲン利用ミニシンポジウム(第9回臭素化学懇話会年会)  2016/11
  • π拡張ジアザポルフィリンの合成  [Not invited]
    井上真奈美, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    2016ハロゲン利用ミニシンポジウム(第9回臭素化学懇話会年会)  2016/11
  • BCOD骨格を有する核置換ヘキサフィリン(1.0.0.1.0.0)の合成  [Not invited]
    小積遼平, 森 重樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
    2016年日本化学会中国四国支部大会  2016/11
  • Synthesis of Nonplanar Octaphenyltetrabenzoporphyrin Phosphorus Complexes  [Not invited]
    村松航太, 三上晃寛, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    The 2nd International Symposium on the Synthesis and Application of Curved Organic -Molecules & Materials (CURO-Pi II)  2016/09
  • β連結型ジピロール骨格を有する環拡張ポルフィリンの合成と物性  [Not invited]
    日浦暢大, 森 重樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
    第27回基礎有機化学討論会  2016/09
  • アニオンを利用したシクロ[n]ピロール誘導体の合成  [Not invited]
    松本宏樹, 安藤千恵, Saurabh Agrawal, 森 重樹, 久木一朗, 中江隆博, 髙瀬雅祥, 宇野英満, 小林長夫, 奥島鉄雄
    第27回基礎有機化学討論会  2016/09
  • チエノジピロール骨格を有するオクタフィリン(1.0.1.0.1.0.1.0)の合成と物性  [Not invited]
    日浦暢大, 森 重樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
    第32回若手研究者のためのセミナー 化学道場2016  2016/08
  • Structure and physical properties of cyclo[8]pyrrole-polyoxometalate complex  [Not invited]
    松本宏樹, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    Ninth International Conference on Porphyrins and Phthalocyanines (ICPP-9)  2016/07
  • Synthesis and properties of expanded porphyrins composed of -connected 2,2’-dipyrroles  [Not invited]
    日浦暢大, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    Ninth International Conference on Porphyrins and Phthalocyanines (ICPP-9)  2016/07
  • Synthesis and Properties of 1,5-Diazafulvalenes  [Not invited]
    松﨑悠也, 志田陽一, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    Ninth International Conference on Porphyrins and Phthalocyanines (ICPP-9)  2016/07
  • Synthesis of Cyclo[n]pyrroles with Intense NIR Absorptions  [Invited]
    OKUJIMA Tetsuo
    Ninth International Conference on Porphyrins and Phthalocyanines (ICPP-9)  2016/07
  • フェニル基を導入した新規オクタフェニルテトラベンゾポルフィリンリン錯体の合成  [Not invited]
    村松航太, 三上晃寛, 森 重樹, 髙瀬雅祥, 宇野英満, 奥島鉄雄
    第37回光化学若手の会  2016/06
  • Synthesis of the Soluble Precursors of Tetrabenzoporphyrins and Their Application to Organic Field Effect Transistor Based on the Solution Process  [Invited]
    OKUJIMA Tetsuo
    227th ECS Meeting  2015/05
  • Ring-Expanded Porphyrins with No Meso-Bridges  [Invited]
    OKUJIMA Tetsuo
    5th Georgian Bay International Conference on Bioinorganic Chemistry (CanBIC-5)  2015/05
  • 高共役ポルフィリノイドの合成と機能  [Invited]
    奥島 鉄雄
    日本化学会中国四国支部主催愛媛地区化学講演会  2014/12
  • π拡張シクロ[n]ピロールの合成  [Not invited]
    奥島 鉄雄
    2013年日本化学会中国四国支部大会  2013/11
  • 愛大発、塗って作る次世代有機太陽電池  [Invited]
    奥島 鉄雄
    サイエンスカフェ@あいだい「環境とエネルギー問題に挑む新テクノロジー」  2013/03
  • 有機合成的手法にもとづく塗布型有機薄膜太陽電池の開発-有機材料の意義-  [Invited]
    奥島 鉄雄
    平成24年度中国地域太陽電池フォーラム第2回課題検討会  2013/03
  • 塗る太陽電池の開発と実用化★徹底解説~低コスト・大面積化が容易な塗る太陽電池を詳解~  [Invited]
    奥島 鉄雄
    Electric Journal第1461回Technical Seminar  2012/11
  • 塗る太陽電池の開発と実用化★徹底解説~低コスト・大面積化が容易な塗る太陽電池を詳解~  [Invited]
    奥島 鉄雄
    Electric Journal第1011回Technical Seminar  2011/11
  • Retro Diels-Alder strategy for the preparation of -expanded porphyrinoid  [Invited]
    OKUJIMA Tetsuo
    3rd Georgian Bay International Conference on Bioinorganic Chemistry (CanBIC-3)  2011/05
  • 溶けない分子を溶かして使うには?-有機合成を基盤とした材料開発-  [Invited]
    奥島 鉄雄
    若手研究者のためのセミナー 第26回若手化学者のための化学道場  2010/09
  • 有機合成化学を活用した塗布変換型有機半導体デバイス  [Invited]
    奥島 鉄雄
    第1回 有機分子・バイオエレクトロニクスの未来を拓く若手研究者討論会  2010/09

MISC

Industrial Property Rights

  • 特開2011-074161:ジアザポルフィリン化合物又はその塩、半導体材料、膜、電子デバイス、電界効果トランジスタ、及び光電変換素子  2011/04/14
    小野 昇, 奥島鉄雄, 金 光男, 山田容子, 大坪才華, 荒牧晋司, 秋山誠治, 武井 出, 大野 玲, 酒井良正
  • 特開2010-077054:ポルフィセン及びその製造法、フィルム、半導体材料、蛍光色素並びに太陽電池  2010/04/08
    山田容子, 奥島鉄雄, 小野 昇, 葛原大軌
  • 特開2010-045186:フタロシアニン前駆体及びその製造方法、フタロシアニンの製造方法、並びにフタロシアニン膜の製造方法  2010/02/25
    小野 昇, 奥島鉄雄, 平尾敦子, 荒牧晋司, 酒井良正
  • 特開2009-215547:有機顔料前駆体及びそれを用いた有機顔料の製造方法、有機顔料を用いた有機電子素子の製造方法、並びに新規な化合物  2009/09/24
    小野 昇, 平尾敦子, 角井隆功, 荒牧晋司, 奥島鉄雄, 橋本祐介, 秋山誠治
  • 特開2007-320957:ビシクロテトラアザポルフィリン化合物及びそれを用いたテトラアザポルフィリン化合物の製造方法、並びに有機電子デバイス及びその製造方法  2007/09/06
    小野 昇, 奥島鉄雄, 菊池 誠, 荒牧晋司, 酒井良正, 平尾敦子
  • 特開2007-224019:ビシクロポルフィリン化合物、ビシクロピロール化合物、化合物の製造方法、有機半導体及びその製造方法  2007/09/06
    小野 昇, 奥島鉄雄, 荒牧晋司

Awards & Honors

  • 2014/11 有機合成化学協会中国四国支部 Incentive Award from The Chugoku-Shikoku Branch, The Society of Synthetic Organic Chemistry, Japan
     Synthesis and Properties of Conjugated -Electronic Compounds for Organic Advanced Materials 
    受賞者: OKUJIMA Tetsuo
  • 2014/04 The Maruyama Memorial Research Award 2014
     Synthesis and Properties of Conjugated Porphyrinoids for Organic Advanced Materials 
    受賞者: OKUJIMA Tetsuo

Research Grants & Projects

  • 熱変換型色素を用いた塗布型有機薄膜太陽電池の開発
    公益財団法人 泉科学技術振興財団:2018年度研究助成
    Date (from‐to) : 2018/10 -2019/09 
    Author : 奥島 鉄雄
  • 電池材料開発研究ユニット
    平成28年度愛媛大学リサーチユニット:
    Date (from‐to) : 2016/06 -2019/03 
    Author : 御崎洋二, 究代表者, 八尋秀典, 奥島鉄雄, 板垣吉晃, 白旗 崇, 森 重樹
  • 外部刺激変換型単分子素子材料の合成と機能化
    平成25年度科学研究費補助金:新学術領域研究 計画研究「分子アーキテクトニクス」
    Date (from‐to) : 2013/04 -2018/03 
    Author : 宇野英満, 究代表者, 奥島鉄雄, 中江隆博, 高瀬雅祥
  • シクロ[n]ピロール類を用いた近赤外吸収色素の創出と機能開発
    平成26年度科学研究費補助金:基盤C
    Date (from‐to) : 2014/04 -2017/03 
    Author : 奥島 鉄雄
  • 愛大物性研究における知と技の拠点形成
    平成25年度愛媛大学研究活性化事業:拠点形成支援
    Date (from‐to) : 2013/07 -2016/03 
    Author : 内藤俊雄, 代表者, 奥島鉄雄, 山本 貴, 森 重樹, 栗栖牧生, 御崎洋二, 白旗 崇, 八尋秀典, 板垣吉晃
  • 近赤外領域で発光するボロン-ジピロメテン色素の開発
    平成25年度愛媛大学研究活性化事業:萌芽研究
    Date (from‐to) : 2013/07 -2015/03 
    Author : 奥島 鉄雄
  • ビピロールを基本骨格に含む環拡張ポルフィリンの合成と機能開発
    平成24年度科学研究費補助金:若手研究(B)
    Date (from‐to) : 2012/04 -2014/03 
    Author : 奥島 鉄雄
  • 高共役化合物の合成法確立と物性評価
    平成23年度科学研究費補助金:基盤研究(B)
    Date (from‐to) : 2011/04 -2014/03 
    Author : 宇野英満, 代表, 奥島鉄雄, 森 重樹
  • 塗る有機薄膜太陽電池に利用可能な半導体材料の開発
    平成23年度秋愛媛大学研究活性化事業:重点研究
    Date (from‐to) : 2011/12 -2013/03 
    Author : 奥島 鉄雄
  • 近赤外光吸収フィルタの材料開発
    平成23年度愛媛大学研究活性化事業:萌芽研究
    Date (from‐to) : 2011/07 -2013/03 
    Author : 奥島 鉄雄
  • フタロシアニン類の熱変換型潜在色素の開発
    平成22年度JST研究成果最適展開支援事業A-STEP「FSステージ探索タイプ」
    Date (from‐to) : 2010/10 -2011/03 
    Author : 奥島 鉄雄
  • ピロール誘導体を用いた高効率有機発光材料の開発
    平成21年度愛媛大学研究開発支援経費:萌芽的研究
    Date (from‐to) : 2009/04 -2011/03 
    Author : 奥島 鉄雄
  • フタロシアニン類の熱変換型潜在色素の開発
    愛媛大学:平成21年度愛媛大学産業シーズ育成研究支援経費
    Date (from‐to) : 2009/09 -2010/08 
    Author : 奥島 鉄雄
  • 有機薄膜太陽電池を指向した新規π電子系有機材料の合成と機能開発
    平成19年度愛媛大学研究開発支援経費:萌芽的研究
    Date (from‐to) : 2007/04 -2009/03 
    Author : 奥島 鉄雄
  • 共役拡張ポルフィリン類の合成と機能開発
    財団法人 日揮・実吉奨学会:平成19年度財団法人実吉奨学会研究助成
    Date (from‐to) : 2007/09 -2008/09 
    Author : 奥島 鉄雄
  • 共役π電子系材料を用いた有機半導体合成と構造制御
    独立行政法人 科学技術振興機構 JSTイノベーションサテライト高知:JSTイノベーションサテライト高知平成19年度研究成果実用化検討(FS)
    Date (from‐to) : 2007/12 -2008/03 
    Author : 奥島 鉄雄
  • アズレン環を含む新規π系拡張型ピロール環状多量体の合成と機能性の開発
    平成16年度科学研究費補助金:若手研究(B)
    Date (from‐to) : 2004/04 -2007/03 
    Author : 奥島 鉄雄
  • 共役π電子系材料の無機担体上での構造制御
    平成16年度愛媛大学研究開発支援経費:研究推進ラボ
    Date (from‐to) : 2004/04 -2006/03 
    Author : 奥島鉄雄, 代表者, 八尋秀典, 愛媛大学工学部, 林 実(愛媛大学工学部, 宇野英満, 愛媛大学総合科学研究支援センター
  • テトラベンゾポルフィリンを用いた新規有機半導体の開発
    愛媛大学:平成15年度愛媛大学学部長裁量経費
    Date (from‐to) : 2003/04 -2004/03 
    Author : 山田容子, 奥島鉄雄
  • ポルフィリンを核とするπ系拡張分子の合成と多段階酸化還元系の構築
    日本科学協会:平成15年度笹川科学研究助成
    Date (from‐to) : 2003/04 -2004/02 
    Author : 奥島 鉄雄

愛媛大学教員活動実績

教育活動(B)

担当授業科目(B01)

  • 2019, the first semester, under graduate, 現代と科学技術
  • 2019, the first semester, under graduate, 現代と科学技術
  • 2019, the first semester, under graduate, 卒業研究Ⅰ
  • 2019, the first semester, master course, 有機反応化学特論
  • 2019, the first semester, master course, 有機反応化学特論
  • 2019, the first semester, master course, 化学ゼミナールⅠ
  • 2019, the first semester, master course, 化学ゼミナールⅢ
  • 2019, the first semester, master course, 分子科学課題演習I


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