Faculty Profiles - KITAMURA Chitoshi

Papers - KITAMURA Chitoshi

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A double-helical S,C-bridged tetraphenyl-para-phenylenediamine and its persistent radical cation Reviewed

Harada K., Hasegawa C., Matsumoto T., Sugishita H., Kitamura C., Higashibayashi S., Hasegawa M., Suzuki S., Kato S.I.

Chemical Communications 59 ( 10 ) 1301 - 1304 2022.12

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical Communications

A structurally constrained, double-helical S,C-bridged tetraphenyl-para-phenylenediamine (TPPD) has been synthesized. The stable radical cation of the S,C-bridged TPPD was generated by chemical oxidation, and the electron spin was found to be delocalized over the entire π-conjugated framework. The excellent conformational stability of the neutral molecule facilitated the separation of its enantiomers.

DOI： 10.1039/d2cc06144a

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Medium Diradical Character, Small Hole and Electron Reorganization Energies and Ambipolar Transistors in Difluorenoheteroles Reviewed

Mori S., Moles Quintero S., Tabaka N., Kishi R., González Núñez R., Harbuzaru A., Ponce Ortiz R., Marín-Beloqui J., Suzuki S., Kitamura C., Gómez-García C.J., Dai Y., Negri F., Nakano M., Kato S.i., Casado J.

Angewandte Chemie - International Edition 2022.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Angewandte Chemie - International Edition

Four difluorenoheteroles having a central quinoidal core with the heteroring varying as furan, thiophene, its dioxide derivative and pyrrole have shown to be medium character diradicals. Solid-state structures, optical, photophysical, magnetic, and electrochemical properties have been discussed in terms of diradical character, variation of aromatic character and captodative effects (electron affinity). Organic field-effect transistors (OFETs) have been prepared, showing balanced hole and electron mobilities of the order of 10−3 cm2 V−1 s−1 or ambipolar charge transport which is first inferred from their redox amphoterism. Quantum chemical calculations show that the electrical behavior is originated from the medium diradical character which produces similar reorganization energies for hole and electron transports. The vision of a diradical as simultaneously bearing pseudo-hole and pseudo-electron defects might justify the reduced values of reorganization energies for both regimes. Structure-function relationships between diradical and ambipolar electrical behavior are revealed.

DOI： 10.1002/anie.202206680

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Structurally strained cyclic xanthene dimers: A model for rigid crown ether moiety in the reduced graphene oxide framework Reviewed

Keita Kishimoto, Kasane Oda, Jun-ichi Nishida, Chitoshi Kitamura, Takeshi Kawase

Bulletin of the Chemical Society of Japan 94 2216 - 2220 2021.10

Reductive methylation of triphthaloylbenzene: Isolation and characterization of hexamethoxy-trinaphthylene and two unexpected trinaphthylene derivatives Reviewed

Nishida K., Ono K., Kato S.i., Kitamura C.

Tetrahedron Letters 61 ( 43 ) 2020.10

Language：English Publishing type：Research paper (scientific journal) Publisher：Tetrahedron Letters

© 2020 Elsevier Ltd With the aim of developing new π-conjugated materials for application in electronics, the reductive methylation of triphthaloylbenzene is presented. Several new products are obtained: 5,6,11,12,17,18-hexamethoxy-trinaphthylene (1a) and two unexpected compounds, i.e., the corresponding monohydroxy-pentamethoxy-trinaphthylene (1b) and a peculiar trinaphtylene derivative (2) possessing hydroxy, methoxy, carbonyl, and ketal groups and a tetrahydrofuran moiety fused on the core. X-ray crystallographic analysis of 1b and 2 reveals that both compounds exhibit deformed frameworks. The investigation of their optical properties shows that the lowest-energy absorption bands for 1a and 1b are a shoulder band around 350 nm, whereas 2 gives rise to a one broad and weak band at 573 nm. All the molecules have negligible fluorescence. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene into a solution of 2 causes a color change from purple to olive brown, which renders it suitable as a pH indicator.

DOI： 10.1016/j.tetlet.2020.152422

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Synthesis, Structures, and Properties of Neutral and Radical Cationic S,C,C-Bridged Triphenylamines Reviewed International journal

S. Kato, T. Matsuoka, S. Suzuki, M. S. Asano, T. Yoshihara, S. Tobita, T. Matsumoto, C. Kitamura

Organic Letters 22 734 - 738 2020.2

Isolation and characterisation of a stable 2-azaphenalenyl azomethine ylide Reviewed

Katayama K., Konishi A., Horii K., Yasuda M., Kitamura C., Nishida J., Kawase T.

Communications Chemistry 2 ( 1 ) 2019.12

Language：English Publishing type：Research paper (scientific journal) Publisher：Communications Chemistry

© 2019, The Author(s). Although azomethine ylides have been fully exploited as versatile reactive intermediates in dipolar cycloaddition reactions to construct a variety of heterocyclic compounds involving a nitrogen atom, little is known about their structural and electronic properties. Here a method is developed for the preparation, isolation and characterization of a stable 2-azaphenalenyl based azomethine ylide. N-Phenyl-5,8-di-t-butyl-2-azaphenalenyl cannot be isolated because it undergoes rapid dimerization by C–C bond formation at the 1 and 3 positions. In contrast, sterically bulkier N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl can be generated and isolated as deep green crystals under deoxygenated conditions. X-ray crystal analysis of this stable azomethine ylide reveals that its azaphenalenyl skeleton has very small bond alternation and structural deformation. The results of spectroscopic and electrochemical theoretical studies indicate that N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl has electronic features that are similar to those of phenalenyl anion and it possesses an extremely high HOMO energy.

DOI： 10.1038/s42004-019-0236-y

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Synthesis and Characterization of Soluble Directly 2,2′-Linked Tetracene Dimer Reviewed International journal

Honda T., Nagahara M., Taka N., Nishida J., Kawase T., Ono K., Kobayashi T., Naito H., Kitamura C.

European Journal of Organic Chemistry 2019 ( 11 ) 2107 - 2114 2019.3

Language：English Publishing type：Research paper (scientific journal) Publisher：European Journal of Organic Chemistry Participation form：Joint(The main charge)

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim A soluble directly 2,2′-linked tetracene dimer was synthesized. Dimerization of 8-bromo-2,3-dihexyl-5,12-tetracenequinone afforded the corresponding bitetracenequinone, which was converted into a tetracene dimer by sequential addition of 1-hexynyllithium and SnCl 2 /HCl. The synthesized tetracene dimer with four hexyl and four 1-hexynyl groups was highly soluble in CH 2 Cl 2 and THF, and the solutions were unstable under air and room light. The compound was studied by X-ray single crystal analysis, UV/Vis, and fluorescence spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations. In the crystal, two tetracene rings take a coplanar conformation although DFT calculations demonstrated that such a molecular structure is energetically unfavorable. The tetracene dimer had red-shifted absorption maxima and large molar extinction coefficients compared with the corresponding tetracene monomer. The tetracene dimer also showed amphoteric redox properties and p-type semiconducting behavior.

DOI： 10.1002/ejoc.201801333

Scopus

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Controlling the Emergence and Shift Direction of Mechanochromic Luminescence Color of a Pyridine-Terminated Compound Reviewed International journal

Kondo M., Yamoto T., Miura S., Hashimoto M., Kitamura C., Kawatsuki N.

Chemistry - An Asian Journal 14 ( 3 ) 471 - 479 2019.2

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemistry - An Asian Journal Participation form：Joint(The vice charge)

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim In this study, mechanochromic luminescence was induced in a complex of mechano-inactive compounds. Dye/acid complexes containing the same π-conjugated backbones were prepared. While the luminophore showed blue and red shifts in photoluminescence spectra when combined with different acids by grinding, it exhibited slight mechanoresponsiveness itself. Also, compounds with similar molecular backbones to the dye/acid complex were synthesized to clarify the color change mechanism. The compounds showed both blue and red shifts in photoluminescence and diffuse reflectance spectra upon grinding, indicating that mechanochromic luminescence in the hydrogen-bonded complex is like its monomeric analogue and that aggregation structure plays an important role in mechanoresponsive behavior rather than the π-conjugated structure. It was shown that a color change can be mechanically induced by imitating the solid-state aggregation structure of other mechanoresponsive compounds without synthetic modification.

DOI： 10.1002/asia.201801647

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Synthesis and properties of π-extended fluoranthene derivatives from 1,2-diarylacenaphthylene derivatives Reviewed International journal

Matsuura K., Nishida J., Ito T., Yokota R., Kitamura C., Kawase T.

Tetrahedron 75 ( 2 ) 278 - 285 2019.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Tetrahedron Participation form：Joint(The vice charge)

© 2018 Elsevier Ltd Acenaphthylene units work as a useful platform for the synthesis of polycyclic aromatic hydrocarbons (PAH). Three 1,2-diarylacenaphthylene derivatives (9-phenanthryl, 7-t-butyl-2-pyrenyl and 2-naphthyl) were prepared by Suzuki-Miyaura coupling of 1,2-dibromoacenaphthylene with the corresponding boronic acids and ester. The Scholl reaction of the phenanthryl derivative affords a donor-acceptor type fluoranthene derivative possessing a hemi-coronene structure by forming two C–C bonds between phenanthryl groups. The reaction of the pyrenyl derivative allows one C–C bond formation to give a helicene-type fluoranthene derivative. The reaction of the naphthyl derivative provides an asymmetric fluroranthene derivative having an anthracene unit accompanied with one C–C bonding reaction, while a photochemical cyclization followed by dehydroaromatization reaction of the compound gives a symmetric fluoranthene derivative with a [5]helicene structure.

DOI： 10.1016/j.tet.2018.11.056

Scopus

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2,4,5,7,9,10-Hexaethynylpyrenes: Synthesis, Properties, and Self-Assembly Reviewed International journal

Kato S., Kano H., Irisawa K., Yoshikawa N., Yamamoto R., Kitamura C., Nara N., Yamanobe T., Uehara H., Nakamaura Y.

Organic Letters 20 7530 - 7534 2018.12

Fluoranthene and its p-extended diimides: Construction of new electron Reviewed International journal

Ishikawa H., Katayama K., Nishida J., Kitamura C., Kawase T.

Tetrahedron Letters 59 3782 - 3786 2018.9

Microwave-accelerated Z-isomerization of (all-E)-lycopene in tomato oleoresin and enhancement of the conversion by vegetable oils containing disulfide compouds Reviewed International journal

Masaki Honda, Haruka Sato, Munenori Takehara, Yoshinori Inoue, Chitoshi Kitamura, Ryota Takemura, Tetsuya Fukaya, Wahyudiono, Hideki Kanda, Motonobu Goto

Eur. J. Lipd Sci. Tech. 120 1800060 2018.4

Synthesis and properties of a decacyclene monoimide and a naphthalimide derivative as three-dimensional acceptor-donor-acceptor systems Reviewed International journal

Yuma Yamamoto, Miu Yoshida, Takuya Morii, Jun-ichi Nishida, Chitoshi Kitamura, Takeshi Kawase

Chem. Asian J. 13 790 - 798 2018.2

Crystal structures of 1-hydroxy-4-propyloxy-9,10-anthraquinone and its acetyl derivative Reviewed International journal

Hidemi Nakagawa and Chitoshi Kitamura

Acta Crystallographica Section E 73 1845 - 1849 2017.12

Constrution of new fluorophores by Diels-Alder reaction of diacenaphthothiophenes Reviewed International journal

Yuma Yamamoto, Yoshiaki Fukuoka, Jun-ichi Nishida, Chitoshi Kitamura, and Takeshi Kawase

Tetrahedron 73 5725 - 5730 2017.9

π-Extended Fluoranthene Imide Derivatives: Synthesis, Structures, and Electronic and Optical Properties Reviewed International journal

Ikumi Kawajiri, Masaya Nagahara, Hiroyuki Ishikawa, Yuma Yamamoto, Jun-ichi Nishida, Chitoshi Kitamura, and Takeshi Kawase

Canadian Journal of Chemistry 95 371 - 380 2017.4

3,4-Bis(4-formylphenyl)-17,17-di(n-pentyl)tetrabenzo[a,c,g,i]fluorene showing solvatochromism and crystallochromism in fluorescence Reviewed International journal

Masanari Ueki, Yusuke Kimura, Yuma Yamamoto, Chitoshi Kitamura, Hiroshi Ikeda, Mirai Tanaka, Jun-ichi Nishida, Takeshi Kawase

Tetrahedron 73 1170 - 1176 2016.12

Fulvalene Derivativs Containing a Tetrabenzofluorene unit: New nonplanar Fulvalenes with High Electron Affinity Reviewed

Kenta Yamada, Hiroshi Shibamoto, Yusuke Tanigawa, Jun-ichi Nishida, Chitoshi Kitamura, Hiroyuki Kurata, Takeshi Kawase

Synlett 27 2085 - 2090 2016.9

1,4-Dihydroxy-2,3-dinitro-9,10-anthraquinone Reviewed

Wataru Furukawa, Munenori Takehara, Yoshinori Inoue, Chitoshi Kitamura

IUCrData 1 x160906 2016.6

Chiral pyridinium phosphoramide as a dual Brønsted acid catalyst for enantioselective Diels-Alder reaction Reviewed

Yasuhiro Nishikawa, Saki Nakano, Yuu Tahira, Kanako Terazawa, Ken Yamazaki, Chitoshi Kitamura, Osamu Hara

Organic Letters 18 2004 - 2007 2016.5

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Papers - KITAMURA Chitoshi