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

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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

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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

4-(3-Bromopropyloxy)-1-hydroxy-9,10-anthraquinone Reviewed

Natsumi Ohira, Munenori Takehara, Yoshinori Inoue, Chitoshi Kitamura

IUCrData 1 x160753 2016.5

2,7,10,13-Tetra-tert-butyl-N-phenylacenaphtho[1,2-j]fluoranthene-4,5-dicarboximide Reviewed

Hiroaki Ozoe, Chitoshi Kitamura, Jun-ichi Nishida, Takeshi Kawase

IUCrData 1 x160473 2016.3

2,7,10,13-Tetra-tert-butyl-N-phenylacenaphtho[1,2-j]fluoranthene-4,5-dicarboximide Reviewed

Hiroaki Ozoe, Chitoshi Kitamura, Jun-ichi Nishida, Takeshi Kawase

IUCrData 1 x160473 2016

syn-Dicyclopenta[b,g]naphthalene-1,8-dione and its Tetracyanoquinodimethane Derivative: New Electron Acceptors Bearing a π-Extended Indacene Unit Reviewed

6.Hironobu Irie, Jun-ichi Nishida, Chitoshi Kitamura, Hiroyuki Kurata, Takeshi Kawase

Chemsitry Letters 44 ( 1747 ) 1749 2015.12

Crystal structure of 1,4-diethoxy-9,10-anthraquinone Reviewed

Chitoshi Kitamura, Sining Li, Munenori Takehara, Yoshinori Inoue, Katsuhiko Ono, Takeshi Kawase

Acta Crystallographica Section E 71 o504 - o505 2015.7

Solid-state Optical Properties and Crystal Structures of 1,4-Dipropoxy-9,10-anthraquinone Polymorphs Reviewed

Chitoshi Kitamura, Sining Li, Munenori Takehara, Yoshinori Inoue, Katsuhiko Ono, Takeshi Kawase, Kazuhiro J. Fujimoto

Bulletin of the Chemical Society of Japan 88 713 - 715 2015.5

Data Mining with Molecular Design Rules Identifies New Class of Dyes for Dye-sensitised Solar Cells Reviewed

9.Jacqueline Cole, Kian S. Low, Hiroaki Ozoe, Panaqiota Stathi, Chitoshi Kitamura, Hiroyuki Kurata, Petra Rudolf, Takeshi Kawase

Physical Chemistry Chemical Physics 16 26684 - 26690 2014.11

Photosensitized E/Z isomerization of (all-E)-lycopene aiming at practical applications Reviewed

8.Masaki Honda, Haruyuki Igami, Takahiro Kawana, Kento Hayashi, Munenori Takehara, Yoshinori Inoue, Chitoshi Kitamura

Journal of Agricultural and Food Chemistry 62 11353 - 11356 2014.11

Crystal structure of 2-bromo-1,4-dihydroxy-9,10-anthraquinone Reviewed

Wataru Furukawa, Munenori Takehara, Yoshinori Inoue, Chitoshi Kitamura

Acta Crystallographica Section E 70 o1130 2014.10

Acenaphtho[1,2-j]fluoranthene-4,5-dicarboxyimides: A new monoimide showing self-aggregation in chloroform Reviewed

Hiroaki Ozoe, Chitoshi Kitamura, Hiroyuki Kurata, Jun-ichi Nishida, Takeshi Kawase

Chemistry Letters 43 1467 - 1469 2014.9

Alkyl Substituent Effects on Molecular Packing and Optoelectronic Properties of 2,3-Dialkyltetracenes Reviewed

Chitoshi Kitamura, Genki Ohe, Takeshi Kawase, Akinori Saeki, Shu Seki

Bulltin of the Chemical Society of Japan 87 915 - 921 2014.8

Pyreno[4,5-b]furan and Pyreno[4,5-b:9,10-b']difuran Derivatives as New Blue Fluorophores: Synthesis, Structure, and Electronic Properties Reviewed

Taketo Kojima, Ruri Yokota, Chitoshi Kitamura, Hiroyuki Kurata, Mirai Tanak, Hiroshi Ikeda, Takeshi Kawase

Chemistry Letters 43 696 - 698 2014.5

Bicyclo[6.3.0]undecapentaenyl Anion: The Next Higher Homolog of Indenyl Anion with Exceptionally Large Ion-Pairing Effects on its Tropicity Reviewed

Hiroaki Ozoe, Yasutaka Uno, Chitoshi Kitamura, Hiroyuki Kurata, Masaji Oda, John W Jones Jr., Lawrence T Scott, Takeshi Kawase

Chemistry An Asian Journal 9 893 - 900 2014.3

Characterization and Thermal Isomerization of (all-E) Lycopene Reviewed

Munenori Takehara, Masatoshi Nishimura, Yoshinori Inoue, Chitoshi Kitamura, Tsutomu Kumagai, Masaki Honda

Journal of Agricultural and Food Chemistry 62 264 - 269 2014.1

Anthracene-1.4.9,10-tetraone Reviewed

Chitoshi Kitamura, Takeshi Kawase

Acta Crystallographica Section E 69 o1597 2013.10

Function of a Glutamine Synthetase-Like Protein in Bacterial Aniline Oxidation via gamma-Glutamylanilide Reviewed

Masahiro Takeo, Akira Ohara, Shinji Sakae, Yasuhiro Okamoto, Chitoshi Kitamura, Dai-ichiro Kato, Seiji Negoro

JOURNAL OF BACTERIOLOGY 195 ( 19 ) 4406 - 4414 2013.10

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER SOC MICROBIOLOGY

Acinetobacter sp. strain YAA has five genes (atdA1 to atdA5) involved in aniline oxidation as a part of the aniline degradation gene cluster. From sequence analysis, the five genes were expected to encode a glutamine synthetase (GS)-like protein (AtdA1), a glutamine amidotransferase-like protein (AtdA2), and an aromatic compound dioxygenase (AtdA3, AtdA4, and AtdA5) (M. Takeo, T. Fujii, and Y. Maeda, J. Ferment. Bioeng. 85:17-24, 1998). A recombinant Pseudomonas strain harboring these five genes quantitatively converted aniline into catechol, demonstrating that catechol is the major oxidation product from aniline. To elucidate the function of the GS-like protein AtdA1 in aniline oxidation, we purified it from recombinant Escherichia coli harboring atdA1. The purified AtdA1 protein produced gamma-glutamylanilide (gamma-GA) quantitatively from aniline and L-glutamate in the presence of ATP and MgCl2. This reaction was identical to glutamine synthesis by GS, except for the use of aniline instead of ammonia as the substrate. Recombinant Pseudomonas strains harboring the dioxygenase genes (atdA3 to atdA5) were unable to degrade aniline but converted gamma-GA into catechol, indicating that gamma-GA is an intermediate to catechol and a direct substrate for the dioxygenase. Unexpectedly, a recombinant Pseudomonas strain harboring only atdA2 hydrolyzed gamma-GA into aniline, reversing the gamma-GA formation by AtdA1. Deletion of atdA2 from atdA1 to atdA5 caused gamma-GA accumulation from aniline in recombinant Pseudomonas cells and inhibited the growth of a recombinant Acinetobacter strain on aniline, suggesting that AtdA2 prevents gamma-GA accumulation that is harmful to the host cell.

DOI： 10.1128/JB.00397-13

Web of Science

A Theoretical Study of Crystallochromy: Spectral Tuning of Solid-state Tetracenes Reviewed

Kazuhiro J. Fujimoto, Chitoshi Kitamura

The Journal of Chemical Physics 139 084511 - 084511 2013.9

Function of a Glutamine Synthetase-Like Protein in Bacterial Aniline Oxidation via ɤ-Glutamylanilide Reviewed

Masahiro Takeo, Akira Ohara, Shinji Sakae, Yasuhiro Okamoto, Chitoshi Kitamura, Dai-ichiro Kato, Seiji Negoro

Journal of Bacteriology 195 4406 - 4414 2013.9

3,14-Bis(p-nitrophenyl)-17,17-dipentyltetrabenzo[a,c,g,i]fluorene: A New Fluorophore Displaying Both Remarkable Solvatochromism and Crystalline-Induced Emission Reviewed

Yoshiaki Ueda, Yusuke Tanigawa, Chitoshi Kitamura, Hiroshi Ikeda, Yuichi Yoshimoto, Kazuhiko Mizuno, Hiroyuki Kurata, Takeshi Kawase

Chemistry An Asian Journal 8 392 - 399 2013.2

Synthesis of 8-Bromo-5,12-tetracenequinone and 2-Bromotetracene Derivatives Invited Reviewed

Chitoshi Kitamura, Naohiro Taka, Takeshi Kawase

Research on Chemical Intermediates 39 139 - 146 2013.1

9,10-Diiodophenanthrene Reviewed

Ruri Yokota, Chitoshi Kitamura, Takeshi Kawase

Acta Crystallographica Section E 68 o3323 - o3323 2012.9

9,10-Dibromophenanthrene Reviewed

Ruri Yokota, Chitoshi Kitamura, Takeshi Kawase

Actra Crystallographica Section E 68 o3174 2012.9

3,6-Dibromophenanthrene Reviewed

Ruri Yokota, Chitoshi Kitamura, Takeshi Kawase

Acta Crystallographica Section E 68 o3100 2012.8

2,3,6,7-Tetramethoxy-9,10-anthraquinone Reviewed

Akira Ohta, Kazuki Hattori, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito, Chitoshi Kitamura

Acta Crystallographica Section E 68 o2587 2012.8

2,6-Dimethoxy-9,10-anthraquinone Reviewed

Akira Ohta, Kazuki Hattori, Takashi Kobayashi, Hiroyoshi Naito, Takeshi Kawase, Chitoshi Kitamura

Acta Crystallographica Section E 68 o2843 2012.8

Effects of Alkoxy Substitution on the Optical Properties of 9,10-Anthraquinone and Anthracene: 2,3,6,7-Tetrapropoxy-substituted vs. 2,6-Dipropoxy-substituted Derivatives Reviewed

Akira Ohta, Kazuki Hattori, Yui Kusumoto, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito, Chitoshi Kitamura

Chemistry Letters 41 674 - 676 2012.7

Two Identical Nonylphenol Monooxygenase Genes Linked to IS6100 and Some Putative Insertion Sequence Elements in Sphingomonas sp. NP5 Reviewed

Masahiro Takeo, Yoshihiro Maeda, Junko Maeda, Naoki Nishiyama, Chitoshi Kitamura, Dai-ichiro Kato, Seiji Negoro

Microbiology 158 1796 - 1807 2012.6

17,17-Dialkyltetrabenzo[a,c,g,i]fluorenes with Extremely High Solid-state Fluorescent Quantum Yields: Relationship Between Crystal Structure and Fluorescent Properties Reviewed

Chitoshi Kitamura, Yusuke Tanigawa, Takashi Kobayashi, Hiroyoshi Naito, Hiroyuki Kurata, Takeshi Kawase

Tetrahedron 68 1688 - 1694 2012.2

Diacenaphtho[1,2-b;1',2'-d]silole and -pyrrole Reviewed

Yoshiharu Nagasaka, Chitoshi Kitamura, Hiroyuki Kurata, Takeshi Kawase

Chemistry Letters 40 1437 - 1439 2011.12

Octaalkyl Tetracene-1,2,3,4,7,8,9,10-octacarboxylates: Synthesis by Twofold [2 + 2 + 2] Cocyclization and Crystallochromy Reviewed

Chitoshi Kitamura, Akira Takenaka, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Chemical Communications 47 6653 - 6655 2011.6

1,7-Diethyl-4,10-diisopropyltetracene Reviewed

Chitoshi Kitamura, Hiroyuki Kano, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Acta Crystallographica Section E 67 o2611 - 2611 2011.6

Synthesis and Properties of anti/syn-Regioisomeric Mixtures of Alkyl-substituted Tetracenes Reviewed

Chitoshi Kitamura, Hiroyuki Kano, Hideki Tsukuda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Heterocycles 73 1621 - 1629 2011.6

An Indenone Synthesis Involving a New Aminotransfer Reaction and its Application to Dibenzopentalene Synthesis Reviewed

Kenta Katsumoto, Chitoshi Kitamura, Takeshi Kawase

European Journal of Organic Chemistry 　 4885 - 4891 2011.5

Synthesis and Solid-state Optical Properties of 2,3-Dialkyl- and 2,3,8,9-Tetraalkyltetracenes Reviewed

Chitoshi Kitamura, Takuya Ohara, Akio Yoneda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Chemistry Letters 40 58 - 59 2011.1

Crystal Structure of 1,4,5,8-Tetrapentylanthracene Reviewed

Chitoshi Kitamura, Hideki Tsukuda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

X-ray Structure Analysis Online 26 65 - 66 2010.11

Dianaphthopentalenes: Pentalene Derivatives for Organic Thin-film Transistors Reviewed

Takeshi Kawase, Takeru Fujiwara, Chitoshi Kitamura, Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Shoji Shinamura, Hiroki Mori, Eigo Miyazaki, Kazuo Takimiya

Angewandte Chemie International Edtition 49 7728 - 7732 2010.10

An Effective Synthesis of N,N-Dimethylamides from Carboxylic Acids and a New Route from N,N-Dimethylamides to 1,2-Diaryl-1,2-diketones Reviewed

Takashi Kumagai, Tomohiro Anki, Takahiro Ebi, Akihito Konishi, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Kenta Katsumoto, Chitoshi Kitamura, Takeshi Kawase

Tetrahedron 66 8968 - 8973 2010.10

1,4,5,8-Tetra-n-butylanthracene Reviewed

Chitoshi Kitamura, Hideki Tsukuda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Acta Crystallographica Section E 66 o2565 2010.9

1,4,5,8-Tetraisopropylanthracene Reviewed

Chitoshi Kitamura, Hideki Tsukuda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito

Acta Crystallographica Section E 66 o2222 2010.8

Synthesis and Crystal Structures of 1,4,8,11-Tetraalkyl-6,13-diphenylpentacenes Reviewed

Chitoshi Kitamura, Takao Naito, Akio Yoneda, Takeshi Kawase, Toshiki Komatsu

Chemistry Letters 39 771 - 773 2010.7

1,4,7,10-Tetraisoalkyltetracenes: Tuning of Solid-state Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation Reviewed

1,4,7,10-Tetraisoalkyltetracenes: Tuning of Solid-state Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

European Journal of Organic Chemistry 3033 - 3040 2010.6

Synthesis, Optical Properties, and Crystal Structure of 1,4-Dipropyltetracene Reviewed

Chitoshi Kitamura, Chika Matsumoto, Akio Yoneda, Takashi Kobayashi, Hiroyoshi Naito, Toshiki Komatsu

European Journal of Organic Chemistry 　 2571 - 2575 2010.5

Pentaleno[1,2-c:4,5-c']dithiophene Derivatives: First Synthesis, Properties, and a Molecular Structure Reviewed

Akihito Konishi, Takeru Fujiwara, Noriko Ogawa, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Chitoshi Kitamura, Takeshi Kawase

Chemistry Letters 39 300 - 301 2010.3

Synthesis and Crystallochromy of 1,4,7,10-Tetraalkyltetracenes: Tuning of Solid-state Optical Properties of Tetracenes by Alkyl Side-chain Length Reviewed

Chitoshi Kitamura, Yasushi Abe, Takuya Ohara, Akio Yoneda, Takeshi Kawase, Takashi Kobayashi, Hiroyoshi Naito, Toshiki Komatsu

Chemistry A European Journal 16 890 - 898 2010.1

Crystal Structure of anti-1,4,5,8-Tetra-t-butyl-2,3,6,7-tetrahydro-1,4:5,8-diepoxyanthracene Reviewed

Chitoshi Kitamura, Hideki Tsukuda, Takeshi Kawase

X-ray Structure Analysis Online 25 105 - 106 2009.10

Preparation, Crystal Structure, and Solid-state Fluorescence of a CH₂Cl₂-Solvated Crystal of 6,13-Bis(t-butylphenyl)-2,3,9,10-tetrapropoxypentacene Reviewed

Chitoshi Kitamura, Takao Naito, Akio Yoneda, Takashi Kobayashi, Hiroyoshi Naito, Toshiki Komatsu

Chemistry Letters 38 600 - 601 2009.7

Characterization of alkylphenol degradation gene cluster in Pseudomonas putida MT4 and evidence of oxidation of alkylphenols and alkylcatechols with medium-length alkyl chain Reviewed

Masahiro Takeo, Subbuswamy K. Prabu, Chitoshi Kitamura, Makoto Hirai, Hana Takahashi, Dai-ichiro Kato, Seiji Negoro

JOURNAL OF BIOSCIENCE AND BIOENGINEERING 102 ( 4 ) 352 - 361 2006.10

Language：English Publishing type：Research paper (scientific journal) Publisher：SOC BIOSCIENCE BIOENGINEERING JAPAN

Alkylphenols (APs) are ubiquitous contaminants in aquatic environments and have endocrine disrupting and toxic effects on aquatic organisms. To investigate biodegradation mechanisms of APs, an AP degradation gene cluster was cloned from a butylphenol (BP)-degrading bacterium, Pseudomonas putida MT4. The gene cluster consisted of 13 genes named bupBA1A2A3A4A5A6CEH1FG From the nucleotide sequences, bupA1A2A3A4A5A6 were predicted to encode a multicomponent phenol hydroxylase (PH), whereas bupBCEHIFG were expected to encode meta-cleavage pathway enzymes. A partial sequence of a putative NtrC-type regulatory gene, bupR, was also found upstream of the gene bupB. This result indicates that APs can be initially oxidized into alkylcatechols (ACs), followed by the meta-cleavage of the aromatic rings. To confirm this pathway, AP degradation tests were carried out using the recombinant P putida KT2440 harboring the PH genes (bupA1A2A3A4A5A6). The recombinant strain oxidized 4-n-APs with an alkyl chain of up to C7 (<= C7) efficiently and also several BPs including those with an alkyl chain with some degree of branching. Therefore, it was found that PH had a broad substrate specificity for APs with a medium-length alkyl chain (C3-C7). Moreover, the cell extract of a recombinant Escherichia coli harboring bupB (a catechol 2,3-dioxygenase gene) converted 4-n-ACs with an alkyl chain of <= C9 into yellow meta-cleavage products with a maximum absorbance at 379 nm, indicating that the second step enzyme in this pathway is also responsible for the degradation of ACs with a medium-length alkyl chain. These results suggest that MT4 is a very useful strain in the biodegradation of a wide range of APs with a medium-length alkyl chain, which known nonylphenol-degrading Sphingomonas strains have never degraded.

DOI： 10.1263/jbb.102.352

Web of Science

Efficient synthesis and crystal structure of new 1,4-ansa-anthraquinone Reviewed

Chitoshi Kitamura, Jun Fujimoto, Nobuhiro Kawatsuki, Akio Yoneda

HETEROCYCLES 68 ( 10 ) 2171 - + 2006.10

Photoinduced orientation in photo-cross-linkable liquid crystalline polymer film containing tolane moiety

N Kawatsuki, Y Fujii, C Kitamura, A Yoneda

CHEMISTRY LETTERS 35 ( 1 ) 52 - 53 2006.1

Language：English Publishing type：Research paper (scientific journal) Publisher：CHEMICAL SOC JAPAN

Photoinduced orientation of a new photo-cross-linkable liquid crystalline polymer film comprising a 4-methoxycinnamoyloxy group connected with a tolane moiety (PMCT6M) is presented. High molecular reorientation order with a biref"ringence value of 0.27 is achieved by exposing the film to linearly polarized ultraviolet light and subsequent annealing. The required degree of the photoreaction for the effective reorientation is 2-5 mol%. Small amount of photo-cross-linked mesogenic groups controls the thermal enhancement of the molecular reorientation.

DOI： 10.1246/cl.2006.52

Web of Science

Crystal structure of another polymorph of 1,4-anthraquinone Reviewed

Chitoshi Kitamura, Nobuhiro Kawatsuki, Akio Yoneda

Analytical Sciences: X-ray Structure Analysis Online 22 ( 12 ) x293 - x294 2006

Language：English Publishing type：Research paper (scientific journal) Publisher：Japan Society for Analytical Chemistry

The crystal structure of another polymorph of 1,4-anthraquinone was determined. The compound crystallizes in monoclinic, space group P21/n with a = 7.301(1), b = 9.674(2), c = 13.831(2)Å, β = 93.175(8)Å, V = 975.5(3)Å3, Z = 4. There is antiparallel π-π stacking between aromatic rings. The packing arrangement is different from another crystal structure for 1,4-anthraquinone (space group P21/b with a = 8.430(1), b = 19.846(2), c = 5.927(1)Å, γ = 100.21(2)°, CCDC code: COBBIE04). 2006 © The Japan Society for Analytical Chemistry.

DOI： 10.2116/analscix.22.x293

Scopus

Crystal structure of 5,12-diphenyltetracene Reviewed

Chitoshi Kitamura, Chika Matsumoto, Nobuhiro Kawatsuki, Akio Yoneda, Takashi Kobayashi, Hiroyoshi Naito

Analytical Sciences: X-ray Structure Analysis Online 22 ( 1 ) x5 - x6 2006

Language：English Publishing type：Research paper (scientific journal) Publisher：Japan Society for Analytical Chemistry

The crystal structure of 5,12-diphenyltetracene was determined. The compound crystallizes in triclinic form, space group P 1 with a = 8.936(3), b = 11.527(4), c = 11.643(5)Å, α = 112.84(2), β = 107.24(2)o, γ = 64.41(2)o, V = 984.8(6)Å3, Z = 2. The tetracene backbone is not planar but takes a some what twisted conformation. There is π-π stacking between the tetracene moieties. 2006 © The Japan Society for Analytical Chemistry.

DOI： 10.2116/analscix.22.x5

Scopus

Synthesis and Photoinduced Alignment of Photo-cross-linkable Copolymer Liquid Crystals Containing Tolane Side Groups Reviewed

Yuki Kitani, Chitoshi Kitamura, Akio Yoneda, Nobuhiro Kawatsuki

Mol. Cryst. Liq. Cryst. 443 181 - 189 2005

Crystal structure of (1,3-butadiyne-1,4-diyl)-4,4′-bis[7-(3-n-hexyl-2- thienyl)ethynyl-2,1,3-benzothiadiazole] Reviewed

Chitoshi Kitamura, Kakuya Saito, Nobuhiro Kawatsuki, Akio Yoneda, Yoshiro Yamashita

Analytical Sciences: X-ray Structure Analysis Online 21 ( 10 ) x155 - x156 2005

Language：English Publishing type：Research paper (scientific journal) Publisher：Japan Society for Analytical Chemistry

The title compound, C40H34N4S4, crystallizes in the monoclinic system, space group C2/c. The cell parameters are a = 29.888(3)Å, b = 5.1829(5)Å, c = 22.511(2)Å, β = 93.686(5)°, V = 3479.9(5)Å3, and Z = 4. The final R value is 0.056. The molecule, half of which is crystallographically independent, is almost planar and has a transoid-configuration. 2005 © The Japan Society for Analytical Chemistry.

DOI： 10.2116/analscix.21.x155

Scopus

Syntheses and Cation-Binding Abilities of Thiacalix[4]arene Derivative Reviewed

Mikio Ouchi, Tetsuji Mizuno, Tomoyuki Maeda, Nobuhide Ebashi, Chitoshi Kitamura, Akio Yoneda, Mauro Mocerino

Dev. Chem. Eng. Mineral Process. 11 529 - 538 2003

Crystal Structure of 1,4-Dimethoxyanthracene Reviewed

Chitoshi Kitamura, Jun Fujimoto, Mikio Ouchi, Akio Yoneda

Anal. Sci 19 X69 - X70 2003

Optical control of magnetic order in molecule-based magnet Mn(TCNE)(x)center dot y(CH2Cl2) Reviewed

DA Pejakovic, C Kitamura, JS Miller, AJ Epstein

JOURNAL OF APPLIED PHYSICS 91 ( 10 ) 7176 - 7178 2002.5

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER INST PHYSICS

Studies of photoinduced magnetization and photoinduced absorption in molecule-based magnet Mn(TCNE)(x).y(CH2Cl2) (xapproximate to2, ysimilar to0.8, TCNE=tetracyanoethylene) are reported. Optical excitation in the blue region of spectrum leads to increased magnetization, accompanied by changes in the electronic spectrum. These effects are preserved long after illumination, indicating formation of a highly metastable electronic state. Partial reversal of the photoinduced effects is obtained by excitation with lower energy visible light. The results suggest that the photoinduced effects are controlled by two distinct electronic transitions. (C) 2002 American Institute of Physics.

DOI： 10.1063/1.1452704

Web of Science

Photoinduced magnetization in the organic-based magnet Mn(TCNE)(x) center dot y(CH2Cl2) Reviewed

DA Pejakovic, C Kitamura, JS Miller, AJ Epstein

PHYSICAL REVIEW LETTERS 88 ( 5 ) 57202 2002.2

Language：English Publishing type：Research paper (scientific journal) Publisher：AMERICAN PHYSICAL SOC

Photoinduced magnetization in a magnet based on organic species is reported for the first time. Upon optical excitation in the blue region of spectrum, Mn(tetracyanoethylene)(x) . y(CH2Cl2) (x approximate to 2, y similar to 0.8) exhibits increased magnetic susceptibility at temperatures as high as 75 K, accompanied with photo-induced absorption in the visible and infrared spectral regions. These effects are partially reversible by lower energy visible light and fully reversible by thermal treatment. The results suggest trapping of the photoexcited charge in a metastable state with enhanced exchange interaction.

DOI： 10.1103/PhysRevLett.88.057202

Web of Science

Synthesis and Crystal Structure of 4,7-Bis(2-thienylethynyl)-2,1,3-benzothiadiazole Reviewed

Chitoshi Kitamura, Kakuya Saito, Mikio Ouchi, Akio Yoneda, Yoshiro Yamashita

J. Chem. Res. (S) 511 - 513 2002

Synthesis fo Cyclometalateed Palladium(II) and Platinum(II) Complexes Using 2-Substituted 8-Quinolinols Containing C-Donor Atoms and Steric Interaction between the Ligands Reviewed

Shin-ichi Ohfuchi, Chitoshi Kitamura, George R Newkome, Akio Yoneda

Nippon Kagakukaishi (in Japanese) ( 2 ) 201 - 210 2002

Photoinduced Magnetization in Molecule-Based Magnets KxCo[Fe(CN)6]y•zH2O (x=0.13, y=0.77, z=3.54) and Mn(TCNE)x?y(CH2Cl2) (x=2) Reviewed

Dusan A. Pejakovic, Jamie L. Manson, Chitoshi Kitamura, Joel S. Miller, Arthur J. Epstein

Polyhedron 20 ( 11/14 ) 1435 - 1439 2001

Synthesis of 2-(substituted methyl)quinolin-8-ols and their Complexation with Sn(II) Reviewed

Chitoshi Kitamura, Naoyuki Maeda, Noboru Kamada, Mikio Ouchi, Akio Yoneda

J. Chem. Soc., Perkin Trans. 1 ( 5 ) 781 - 785 2000

Synthesis and Crystal Structure of 2, 2'-Dimethyl-8, 8'-biquinolyl Reviewed

Chitoshi Kitamura, Shinya Yamamoto, Mikio Ouchi, Akio Yoneda

J. Chem. Res. (S) 46 - 47 2000

Silver and Thallium Ion Complexation with Allyloxycalix[4]arenes Reviewed

Daniel Couton, Mauro Mocerino, Chris Rapley, Chitoshi Kiamura, Akio Yoneda, Mikio Ouchi

Aust. J. Chem. 52 ( 3 ) 227 - 229 1999

Synthesis of Palldium(II) Cyclometalated Complexes of 2-β-Disubstituted Ethenyl-8-quinolinols and Steric Interactions of Adjacent Substituents on Chelate Ring Stability Reviewed

Shin-ichi Ohfuchi, Chitoshi Kitamura, Yoshihiko Maekawa, George R. Newkome, Akio Yoneda

Nippon Kagakukaishi (in Japanese) ( 3 ) 151 - 160 1999

Bis(2-methyl-8-quinolinolate-N,O) tin(II) Reviewed

Chitoshi Kitamura, Akio Yondeda, Ken-ichi Sugiura, Yoshiteru Sakata

Acta Cryst. Sect. C 55 876 - 878 1999

Studies on New Narrow-Bandgap Polymers Composed of Aromatic-Donor and o-Quinoid-Acceptor Segments Reviewed

Chitoshi Kitamura

1996.3

Design of Narrow-Bandgap Polymers, Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units Reviewed

Chitoshi Kitamura, Shoji Tanaka, Yoshiro Yamashita

Chem. Mater. 8 ( 2 ) 570 - 578 1996

New Narrow-Bandgap Polymers Composed of[1,2,5]Thiadiazolo[3,4-g]quinoxaline and Aromatic Heterocycles Reviewed

Chitoshi Kitamura, Shoji Tanaka, Yoshiro Yamashita

Chem. Lett. ( 1 ) 63 - 64 1996

New Narrow-Bandgap Polymer Composed of Benzobis(1,2,5-thiadiazole)and Thiophenes Reviewed

Michinori Karikomi, Chitoshi Kitamura, Shoji Tanaka, Yoshiro Yamashita

J. Am. Chem. Soc. 117 ( 25 ) 6791 - 6792 1995

Synthesis of New Narrow Bandgap Polymers Based on 5,7-Di(2-thienyl)thieno[3,4-b]pyrazine and its Derivatives

Chitoshi Kitamura, Shoji Tanaka, Yoshiro Yamashita

J. Chem. Soc., Chem. Commun. ( 13 ) 1585 - 1586 1994

Formation of Radical Cation and Dication of 1,3,4,6-Tetrakis(isopropyl)-2λ4δ2-thieno[3,4-C]thiophene and their Reactions with Nucleophiles Reviewed

Akira Tsubouchi, Chitoshi Kitamura, Noboru Matsumura, Hiroo Inoue

J. Chem. Soc., Perkin Trans. 1 2935 - 2940 1991

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