Papers - Kurata Hiroyuki

Synthesis, Chiroptical Properties, and Absolute Configuration Determination of Phenyl-4-pyridyl-2,5-dipyrimidinylmethaneDecomposition of Unpolarized Reviewed International coauthorship International journal

Kouzou Matsumoto, Rina Tanaka, Kaori Miki, Akihito Konishi, Hiroyuki Kurata, Takashi Kubo, Gennaro Pescitelli, Koichi Matsuo, and Tatsuo Nehira

Asian Journal of Organic Chemistry   e202400577   2024.11

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Phenyl-4-pyridyl-2,5-dipyrimidinylmethane (1) has been synthesized in five steps from 5-methylpyrimidine. The structural feature of 1 is the symmetry elements with respect to the 180° rotation of the aryl group along the central C−C bonds. Due to this structural feature, the compound 1 is expected the good crystallinity despite of the asymmetric molecular structure. The optical resolution of 1 was achieved by high performance liquid chromatography using chiral stationary phase (chiral HPLC). The circular dichroism (CD) spectra of the two fractions showed opposite signs. As expected, the X-ray crystallographic analysis was successfully performed for both the racemic and enantiomerically pure crystals of 1, with the nitrogen atoms being unambiguously assigned in both cases. It was concluded the first-eluted fraction in chiral HPLC was determined to be S configuration both by the CD calculation for reproducing the experimental CD spectrum and by the anomalous diffraction of X-ray crystallographic analysis of enantiomerically pure 1.

Decomposition of Unpolarized Fluorescence Spectrum of Uniaxially Oriented 1,3,5‑Triphenylbenzene Microcrystals Into Polarized Fluorescence Spectra Reviewed International journal

Michihiro Hara, Tatsuya Takeshita, Hiroyuki Kurata, Tsunehisa Kimura

Journal of Fluorescence   33   1559 - 1563   2023.2

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Luminescence from solids such as crystals and aggregates is of growing academic and industrial interest. In this study, we report decomposition of the unpolarized fluorescence spectrum of uniaxially oriented 1,3,5-triphenylbenzene (TPB) microcrystals into four polarized spectra measured with polarizer (V: vertical and H: horizontal) and analyzer (V: vertical and H: horizontal), where V and H indicate perpendicular and parallel to the layer of TPB molecules in the crystal, respectively. Resolved spectra were interpreted in terms of the molecular and excimer like (J- and H-dimer) emissions. The origin of the excimer like emissions was discussed in relation to the molecular packing in the crystal. It was shown that polarized crystal fluorescence can provide insight into the excitation/emission process in the crystal. Although preliminary, this study demonstrates the potential of polarized fluorescence to elucidate the luminescent mechanism.

Unexpected formation of (Z)-1,2-bis(5-fluoropyridin-2-yl)diazene 1-oxide by oxidation of 2-amino-5-fluoropyridine

Kouzou Matsumoto, Hiroyuki Kurata

Bulletin of the Institute of Natural Sciences Senshu University   ( 53 )   55 - 59   2022.3

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When we tried to synthesize 5-fluoro-2-nitropyridine (1) by the corresponding amino derivative with hydrogen peroxide, (Z)-1,2-bis(5-fluoropyridin-2-yl)diazene 1-oxide (2) was obtained as a by-product. By modification of the reaction conditions, 2 was mainly obtained in moderate yield. The spectroscopic properties and X-ray crystallographic analysis of 2 are also presented.

Thermogravimetric analysis and crystal structure of tri-3-pyridylmethanol monohydrate

Kouzou Matsumoto, Hiroyuki Kurata, Disuke Takajo

Bulletin of the Institute of Natural Sciences Senshu University   52   59 - 63   2021.3

Asymmetric amination of meso-epoxide with vegetable powder as a low-toxicity catalyst Reviewed

Yuki Takeuchi, Tatsuhiro Asano, Kazuya Tsuzaki, Koichi Wada,; Hiroyuki Kurata

Molecules   25 ( 14 )   3197 - 3209   2020.7

Chiral Tetraarylmethane Derivative with Metal‐Coordinating Ability Reviewed

Kouzou Matsumoto, Kaori Miki, Rina Tanaka, Takahiro Matsuda, Tatsuo Nehira, Yasukazu Hirao, Hiroyuki Kurata, Gennaro Pescitelli, Takashi Kubo

Asian Journal of Organic Chemistry   9 ( 4 )   652 - 659   2020.1

Selective Mono-Bromination of 2,2'-Bithiophene Using a Flow Microreactor Reviewed

Hiroyuki Kurata

Memoirs of Fukui University of Technology   47   129 - 136   2017.5

Syntheses of Partially Brominated Derivatives of Tetra-2-thienylmethane for Three-Dimensionally Extended pai-Electron Systems Reviewed

Kouzou Matsumoto, Takeshi Suzuki, Yasukazu Hirao, Hiroyuki Kurata, Takashi Kubo

Heterocycles   95 ( 1 )   615 - 623   2016.11

Synthesis, Structure, and Properties of Quinone Methides Incorporating Thiophene and Bithiophene Derivatives: New Overcrowded Extended Quinonoid π-Systems Invited Reviewed

Hiroyuki Kurata, Taihei Inoue, Takeshi Suzuki, Yasukazu Hirao, Kouzou Matsumoto, Takashi Kubo

Synlett   27 ( 14 )   2133 - 2139   2016.6

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チオフェンおよびビチオフェンの全てのCH部にキノメチドが導入された新規な非平面性キノメチド誘導体を合成し，それらの構造，物性を明らかにした。

Fulvalene Derivatives Containing a Tetrabenzofluorene Unit: New Nonplanar Fulvalenes with High Electron Affinity Invited Reviewed

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

Synlett   27 ( 14 )   2085 - 2090   2016.6

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テトラベンゾフルオレン骨格を有するフルバレン誘導体を合成した。これらは新規な非極性フルバレン誘導体であり，高い電子受容能を持つことが明らかになった。

2,3-Diphenylphenanthro[9,10-b]furan Derivativesas New Blue Fluorophores Reviewed

Taketo Kojima, Ikumi Kawajiri, Jun-ichi Nishida, Chitoshi Kitamura, Hiroyuki Kurata, Mirai Tanaka, Hiroshi Ikeda, Takeshi Kawase

Bulletin of the Chemical Society of Japan   89 ( 2 )   931 - 940   2016.5

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2,3-ジフェニルフェナンスロ[9,10-b]フランおよびその誘導体を合成し，それらが新規な青色発光体として機能することを明らかにした。

Synthesis, Molecular Structure, and Morphological Properties of Dendritic Tetra-2-Thienylmethane Reviewed

Kouzou Matsumoto, Sota Kugo, Takeshi Suzuki, Daisuke Takajo, Akira Inaba, Yasukazu Hirao, Hiroyuki Kurata, Takashi Kubo

Heterocycles   91 ( 12 )   2343 - 2353   2015.11

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デンドリマー状に拡張したテトラキス(2-チエニル)メタン誘導体を合成し，それらの性質を明らかにした。

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

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

Chemistry Letters   44 ( 12 )   1747 - 1749   2015.10

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syn-ジシクロペンタ[b,g]ナフタレン-1,8-ジオンおよびそのテトラシアノキノジメタン誘導体を合成し，それらが拡張インダセン骨格を有する優れた電子受容体であることを明らかにした。

A facile synthesis of trinaphtho[3.3.3]propellane and its π-extension and the formation of a two-dimensional honeycomb molecular assembly Reviewed

Takashi Kubo, Shogo Miyazaki, Takuya Kodama, Mitsuya Aoba, Yasukazu Hirao, Hiroyuki Kurata

Chemical Communications   51 ( 18 )   3801 - 3803   2015.1

Synthesis of Nickel(II) Cage Complex with mew2-Cl Bridging Reviewed

Kouzou Matsumoto, Naoki Kitayama, Yasukazu Hirao, Hiroyuki Kurata, and Takashi Kubo

Heterocycles   93 ( 1 )   406 - 410   2015.1

Isolation of a Hydrogen-Bonded Complex Based on the Anthranol/Anthroxyl Pair: Formation of a Hydrogen-Atom Self-Exchange System Reviewed

Yasukazu Hirao, Tohru Saito, Hiroyuki Kurata, and Takashi Kubo

Angewandte Chemie, International Edition   54 ( 8 )   2402 - 2405   2015.1

Synthesis of Sexithiophene-Bridged Cage Compound: A New Class of Three-Dimensionally Expanded Oligothiophenes Reviewed

Kazuhiko Adachi, Yasukazu Hirao, Kouzou Matsumoto, Takashi Kubo, and Hiroyuki Kurata

Organic Letters   16 ( 22 )   5870 - 5873   2014.10

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3つのセキシチオフェン鎖からなるビシクロ型かご状化合物の合成に成功し，その構造をNMRスペクトル, 高分解能質量スペクトル,X線結晶構造解析より明らかにした。電子スペクトルにおいて，ひずみのあるかご構造に基づく短波長シフトを示し，電気化学的分析において3次元的に固定されたセキシチオフェン鎖同士の分子内の相互作用が観測された。

Efficient Synthesis of Tetrakis(4-pyridyl)methane: Pyrolysis of 4-pyridylazo(4-pyridyl)methane Reviewed

Daisuke Inokuchi, Kouzou Matsumoto, Kenji Kobayashi, Koji Onishi, Yasukazu Hirao, Hiroyuki Kurata, Takashi Kubo

Chemistry Letters   44 ( 1 )   32 - 34   2014.10

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テトラキス(4-ピリジル)メタンの簡便な合成法を開発した。4-ピリジルアゾ(4-ピリジル)メタンの熱分解によって中程度の収率ながらこれまで煩雑な過程を必要としていたテトラキス(4-ピリジル)メタンをグラムスケールで得ることに成功した。

Acenaphtho[1,2-j]fluoranthene-4,5-dicarboxyimides: A New Monoimide Showing Self-aggregation in Chloroform Reviewed

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

Chemistry Letters   43 ( 9 )   1467 - 1469   2014.9

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標題化合物をジアセナフト縮環チオフェン誘導体と無水マレイン酸との環化付加反応およびそれに続くアミン類との反応により合成した。無水マレイン酸との反応では2分子付加体も得られ，その物質は溶液中で強い蛍光を示した。イミド体は結晶状態では黄色であるが，アモルファス状態では赤色を示す。

Design and Synthesis of New Stable Fluorenyl-Based Radicals Reviewed

Yi Tian , Kazuyuki Uchida , Hiroyuki Kurata , Yasukazu Hirao , Tomohiko Nishiuchi , Takashi Kubo

Journal of the American Chemical Society   136 ( 36 )   12784 - 12793   2014.8

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フルオレニルを基盤とした新規な長寿命炭素ラジカル種を3種合成した。密度汎関数による理論計算と，X線結晶構造解析，電子スピン共鳴スペクトル，電子核二重共鳴スペクトル，紫外可視－近赤外吸収スペクトル等の実験手法によってその構造，物性を明らかにした。