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Library construction and luminescence property analysis of the pi-electronic molecules exhibiting polymorph-dependent luminescence

Research Project

Project/Area Number 16K05743
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional solid state chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

MUTAI Toshiki  東京大学, 生産技術研究所, 助教 (80313112)

Co-Investigator(Kenkyū-buntansha) 重光 保博  長崎大学, 工学研究科, 教授 (50432969)
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords蛍光 / 結晶工学 / ナノ構造 / ESIPT / プロトン移動 / イミダゾピリジン / 固体発光材料 / 固体発光 / 水素結合 / 結晶多形 / ESIPT蛍光 / 有機結晶 / 結晶構造 / 蛍光発光 / 計算化学 / 光物性 / 有機化学
Outline of Final Research Achievements

"Polymorph-Dependent Luminescence (PDL)" has attracted attention because it can control the solid-state luminescence property through the molecular aggregation structure without changing the chemical structure of the molecule, however the detailed mechanism is yet to be cleared. In this project, firstly, a group of compounds having the "identical" light-emitting unit suitable for examining the mechanism of PDL was prepared. Furthermore, femtosecond transient absorption measurements and computational chemistry strongly suggested that the luminescent species in the PDL crystal is a complex composed of two molecules, by which we concluded that the difference in the structure of this complex is an important factor in displaying PDL.

Academic Significance and Societal Importance of the Research Achievements

固体有機発光材料は身近な材料であり、発光色など各種物性は合成化学的に分子構造を変えることで制御されている。近年、合成化学の技術によらず有機分子の「集まり方」を変えることで発光特性を制御できる、という研究成果が世界各地から報告されているが、その発光機構の詳細はいまだ明らかではない。
本研究は、機構解明に向けた適切な分子群を提供することができたことが第一の成果で、さらに、この発光機構を分子レベルで明らかにする重要な手がかりとなる成果を得ることに成功した。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (35 results)

All 2019 2018 2017 2016

All Journal Article (16 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 13 results,  Acknowledgement Compliant: 3 results,  Open Access: 3 results) Presentation (18 results) (of which Int'l Joint Research: 1 results,  Invited: 5 results) Book (1 results)

  • [Journal Article] Re-evaluation of the tert-Butyl Method in Crystal Engineering of Salicylideneanilines by Simultaneous Observation of Photochromism and Thermochromism in Single Crystals2019

    • Author(s)
      Houjou Hirohiko、Kato Taku、Huang Hongyi、Suzuki Yoshikazu、Yoshikawa Isao、Mutai Toshiki
    • Journal Title

      Crystal Growth & Design

      Volume: 19 Issue: 2 Pages: 1384-1390

    • DOI

      10.1021/acs.cgd.8b01764

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spectroscopic properties of push-pull 2-(4-carboxyphenyl-6-dimethylaminobenzothiazole derivatives in solution and the solid state2019

    • Author(s)
      Takahashi, Yusuke; Uehara, Takuya; Matsuhashi, Chihiro; Yamaji, Minoru; Mutai, Toshiki; Yoshikawa, Isao; Houjou, Hirohiko; Kitagawa, Kota; Suenobu, Tomoyoshi; Maki, Shojiro; Hirano, Takashi
    • Journal Title

      Journal of Photochemistry and Photobiology, A: Chemistry

      Volume: 376 Pages: 324-332

    • DOI

      10.1016/j.jphotochem.2019.03.021

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Imidazo[1,2-a]pyridine Derivatives with an Intramolecular Hydrogen-Bonded Seven-Membered Ring Exhibiting Bright ESIPT Luminescence in the Solid State2019

    • Author(s)
      Mutai Toshiki、Muramatsu Tatsuya、Yoshikawa Isao、Houjou Hirohiko、Ogura Masaru
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 7 Pages: 2143-2146

    • DOI

      10.1021/acs.orglett.9b00455

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Excited-state Intramolecular Proton Transfer Process of Crystalline 6-Cyano-2-(2'-hydroxyphenyl)imidazo[1,2a]Prydine, as Revealed by Femtosecond Pump-Probe Microspectroscopy2019

    • Author(s)
      Yukihide Ishibashi, Mako Murakami, Koji Araki, Toshiki Mutai, Tsuyoshi Asahi
    • Journal Title

      J. Phys. Chem. C,

      Volume: 印刷中 Issue: 17 Pages: 11224-11232

    • DOI

      10.1021/acs.jpcc.9b01044

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 固体ESIPT発光材料の新展開2019

    • Author(s)
      務台 俊樹
    • Journal Title

      光化学

      Volume: 50 Pages: 10-16

    • NAID

      40021890097

    • Related Report
      2018 Annual Research Report
  • [Journal Article] 外部刺激により可逆スイッチング可能な有機多形依存型発光2018

    • Author(s)
      務台俊樹
    • Journal Title

      化学工業

      Volume: 69 Pages: 24-29

    • Related Report
      2017 Research-status Report
  • [Journal Article] Dinuclear fused salen complexes of group-10 metals: Peculiarity of the crystal structure and near-infrared luminescence of a bis(Pt-salen) complex2017

    • Author(s)
      Houjou Hirohiko、Hoga Yuki、Ma Yi-Lan、Achira Hiroto、Yoshikawa Isao、Mutai Toshiki、Matsumura Kazunari
    • Journal Title

      Inorganic Chimica Acta

      Volume: 461 Pages: 27-34

    • DOI

      10.1016/j.ica.2017.01.031

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effects of interaction between the chelate rings and π-conjugated systems in fused salphen complexes on UV-Vis-NIR spectra2017

    • Author(s)
      Houjou Hirohiko、Yagi Keisuke、Yoshikawa Isao、Mutai Toshiki、Araki Koji
    • Journal Title

      Journal of Physical Organic Chemistry

      Volume: 30 Issue: 6

    • DOI

      10.1002/poc.3635

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of salicylaldehydes fine-tuned by modular assembly using "plug-and-socket" type extendibility2017

    • Author(s)
      Hirohiko Houjou, Yoshikazu Suzuki, Qian-Wen Shen, Isao Yoshikawa, Toshiki Mutai
    • Journal Title

      Chem. Eur. J.

      Volume: 印刷中 Issue: 34 Pages: 8286-8294

    • DOI

      10.1002/chem.201701141

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes2017

    • Author(s)
      Shota Fujino, Minoru Yamaji, Hideki Okamoto, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou, Fumito Tani
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 印刷中 Issue: 6 Pages: 925-934

    • DOI

      10.1039/c7pp00040e

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Excited-State Intramolecular Proton Transfer and Global Aromaticity2017

    • Author(s)
      Naoko Nishina, Toshiki Mutai, Jun-ichi Aihara
    • Journal Title

      J. Phys. Chem. A

      Volume: 121 Issue: 1 Pages: 151-161

    • DOI

      10.1021/acs.jpca.6b11684

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 固体で高効率発光を示すイミダゾピリジン誘導体の合成 ― ESIPT発光特性とその結晶構造依存性2017

    • Author(s)
      務台 俊樹,荒木 孝二
    • Journal Title

      有機合成化学協会誌

      Volume: 74 Pages: 330-339

    • NAID

      130005627978

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] A comparative study of the electronic spectra, fluorescence quantum yields, voltammograms and theoretical caliculations of phenanthrene-type benzodifurans2016

    • Author(s)
      N. Hayashi, Y. Saito, X. Zhou, J. Yoshino, H. Higuchi, T. Mutai
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 29 Pages: 4159-4168

    • DOI

      10.1016/j.tet.2016.05.019

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Effects of Semi-flexible Linker on Mechanochromic Photoluminescence of a Bis(Pt-salen) Complex2016

    • Author(s)
      Hirohiko Houjou, Keisuke Yagi, Isao, Yoshikawa, Toshiki Mutai, Koji Araki
    • Journal Title

      Polyhedron

      Volume: 未定 Pages: 123-131

    • DOI

      10.1016/j.poly.2016.04.022

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Development of Aryl-substituted 2-Phenylimidazo[1,2-a]pyridines (PIP) with Various Colors of Excited-State Intramolecular Proton Transfer (ESIPT) Luminescence in the Solid State2016

    • Author(s)
      Toshiki Mutai, Tatsuya Ohkawa, Hideaki Shono, Koji Araki
    • Journal Title

      J. Mater. Chem. C

      Volume: 4 Issue: 16 Pages: 3599-3606

    • DOI

      10.1039/c6tc00376a

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 有機超分子の発光 -分子をどのように集め光らせるか-2016

    • Author(s)
      務台 俊樹
    • Journal Title

      日本写真学会誌

      Volume: 79 Pages: 319-322

    • NAID

      130006258103

    • Related Report
      2016 Research-status Report
    • Open Access / Acknowledgement Compliant
  • [Presentation] 分子内水素結合を含む七員環を有するイミダゾピリジン誘導体の固体発光と置換基効果2019

    • Author(s)
      鈴木 陸人, 務台 俊樹, 吉川 功, 北條 博彦, 小倉 賢
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 有機超分子の発光化学 結晶多形を利用して固体発光を制御する2018

    • Author(s)
      務台 俊樹
    • Organizer
      近畿大学総合理工学研究科 第13回光エネルギーセミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 分子内水素結合を介した七員環を有するイミダゾピリジン誘導体の固体発光特性2018

    • Author(s)
      務台 俊樹, 村松 達也, 吉川 功, 北條 博彦, 小倉 賢
    • Organizer
      2018光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ESIPT 発光を示す分子内水素結合7 員環化合物の電子状態解析2018

    • Author(s)
      重光 保博, 務台 俊樹
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ヒドロキシフェニルイミダゾ[1,2-a]ピリジン誘導体の集積構造依存発光特性と2分子間相互作用に関する理論的研究2018

    • Author(s)
      三木 伸一, 重光 保博, 務台 俊樹
    • Organizer
      第41回ケモインフォマティクス討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 七員環型分子内水素結合を有する縮環イミダゾールの固体発光特性2018

    • Author(s)
      務台 俊樹, 村松 達也, 吉川 功, 北條 博彦, 小倉 賢
    • Organizer
      第27回日本化学会有機結晶シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子内水素結合を含む七員環を有するイミダゾピリジン誘導体の結晶構造依存性発光2018

    • Author(s)
      村松達也、小倉賢、吉川功、北條 博彦、務台俊樹
    • Organizer
      第98日本化学会春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Organic supramolecules showing stimuli-responsive luminescence2017

    • Author(s)
      Toshiki MUTAI
    • Organizer
      Feringa Academic Alumni Symposium, Chemistry for the Future
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 分子内水素結合を介した七員環を形成するイミダゾ[1,2-a]ピリジン誘導体の結晶構造と発光特性2017

    • Author(s)
      務台俊樹、村松達也、吉川功、北條 博彦、小倉賢
    • Organizer
      第26回有機結晶シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] アントラキノン-ホウ素錯体の振電相互作用解析2017

    • Author(s)
      三木伸一、重光保博、松居正樹
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Research-status Report
  • [Presentation] クロロフェニルイミダゾ[1,2-a]ピリジン誘導体の集積構造依存発光の理論解析2017

    • Author(s)
      三木伸一、重光保博、務台俊樹
    • Organizer
      第47回 複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 6-Cyano-2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine結晶のフェムト秒顕微過渡吸収分光2017

    • Author(s)
      石橋 千英, 村上 眞子, 務台 俊樹, 荒木 孝二, 朝日 剛
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應大学(神奈川県横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] 結晶を温める・すりつぶす ~ 発光がスイッチングする有機結晶2016

    • Author(s)
      務台 俊樹
    • Organizer
      第6回CSJ化学フェスタ2016(日本化学会)
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 有機超分子の発光化学2016

    • Author(s)
      務台 俊樹
    • Organizer
      城西大学セミナー
    • Place of Presentation
      城西大学(埼玉県坂戸市)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 有機超分子の発光 -分子をどのように集め、光らせるか-2016

    • Author(s)
      務台 俊樹
    • Organizer
      第13回 日本写真学会光機能性材料セミナー -光機能性を活かす構造制御技術-
    • Place of Presentation
      東京工芸大学(東京都中野区)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 6-Cyano-2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridine結晶の蛍光ダイナミクス2016

    • Author(s)
      村上 眞子, 石橋 千英, 務台 俊樹, 荒木 孝二, 朝日 剛
    • Organizer
      2016年日本化学会中四国支部大会
    • Place of Presentation
      香川大学(香川県高松市)
    • Related Report
      2016 Research-status Report
  • [Presentation] 分子内および分子間水素結合部位を有するイミダゾピリジン誘導体の固体ESIPT発光2016

    • Author(s)
      金田 祥平, 吉川 功, 北條 博彦, 務台 俊樹
    • Organizer
      2016光化学討論会
    • Place of Presentation
      東京大学駒場キャンパス(東京都目黒区)
    • Related Report
      2016 Research-status Report
  • [Presentation] アリール基を用いたイミダゾ[1,2-a]ピリジンの固体ESIPT発光の段階的制御とその機構2016

    • Author(s)
      務台 俊樹, 大川 達也, 生野 秀明, 荒木 孝二
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島県広島市)
    • Related Report
      2016 Research-status Report
  • [Book] 光化学フロンティア2018

    • Author(s)
      水野 一彦、宮坂 博、池田 浩
    • Total Pages
      400
    • Publisher
      化学同人
    • ISBN
      9784759814194
    • Related Report
      2018 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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