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Control of the crytal structure and analyses of the emission mechanism of heterocyclic compounds based on the distorted conformation of their hydrogen-bonding ring

Research Project

Project/Area Number 19K05434
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
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) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2021: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords固体発光 / 有機結晶 / ESIPT / 蛍光材料 / 超弾性 / メカノクロミック発光 / 結晶多形 / 水素結合 / 蛍光 / イミダゾピリジン / メカノクロミズム / 七員環 / 分子内水素結合 / 結晶構造解析 / 計算化学 / 励起状態解析
Outline of Research at the Start

分子の集まり方によって固体発光の色や強度が変化する「集積構造依存型発光」は、分子の化学構造を変えずに発光を制御できる系として近年注目されている。
本研究では、この発光の制御因子として"ひずみ環構造"を利用することを提案し、分子の集積構造や電子状態に与える効果の測定・検証を通じて、その有用性を明らかにすることを目的とする。さらに熱や圧力、溶媒などの外部刺激により発光スイッチングを示す新しい有機固体光機能材料への展開を目指す。

Outline of Final Research Achievements

We have shown that the introduction of "distorted intramolecular hydrogen bond" led to a certain degree of conformational freedom and may have made the polymorphism easier to occur. In the course of our research, we also discovered a mechanochromic luminescence phenomenon based on a nondestructive reversible crystal-crystal phase transition called "superelastochromic luminescence," and attempted crystal structure analysis of excited states, which has been considered difficult to measure until now, and succeeded in observing the conformational change These achievements are the result of our research on organic solid-state luminescence materials. These results are important findings for mechanistic analysis and material development of organic solid-state light-emitting materials.

Academic Significance and Societal Importance of the Research Achievements

有機固体発光材料は身近な材料であり、多くの場合、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し、また「超弾性発光クロミズム」という新たな発光制御方法を見出すとともに、励起状態でのX線結晶構造解析という、発光機構の解析に向けた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)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (21 results)

All 2022 2021 2020 2019 Other

All Journal Article (10 results) (of which Peer Reviewed: 8 results,  Open Access: 3 results) Presentation (9 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Organic soft crystals exhibiting spontaneously reversible mechano-responsive luminescence2022

    • Author(s)
      Mutai Toshiki、Takamizawa Satoshi
    • Journal Title

      Journal of Photochemistry and Photobiology C: Photochemistry Reviews

      Volume: 51 Pages: 100479-100479

    • DOI

      10.1016/j.jphotochemrev.2021.100479

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 分子性有機結晶の超弾性発光クロミズム2022

    • Author(s)
      務台俊樹
    • Journal Title

      光化学

      Volume: 53 Pages: 29-32

    • Related Report
      2021 Annual Research Report
  • [Journal Article] Time-Resolved X-ray Crystallography Using Synchrotron Radiation2021

    • Author(s)
      SATO-TOMITA Ayana、UMENA Yasufumi、ICHIYANAGI Kouhei、FUKAYA Ryo、HIKTA Masahide、MATSUGAKI Naohiro、MUTAI Toshiki
    • Journal Title

      Nihon Kessho Gakkaishi

      Volume: 63 Issue: 1 Pages: 24-30

    • DOI

      10.5940/jcrsj.63.24

    • NAID

      130007994790

    • ISSN
      0369-4585, 1884-5576
    • Year and Date
      2021-02-28
    • Related Report
      2021 Annual Research Report
    • Open Access
  • [Journal Article] Computational Investigation on ESIPT-driven Luminescence of Imidazo[1,2-a]pyridine Derivatives Regulated by Inter/Intramolecular Hydrogen bonding2021

    • Author(s)
      Shigemitsu Yasuhiro、Muramatsu Tatsuya、Mutai Toshiki
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 409 Pages: 113140-113140

    • DOI

      10.1016/j.jphotochem.2021.113140

    • NAID

      120006956177

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, characterization of calix[5]azulene and its complexation with pyridinium salts2021

    • Author(s)
      Jin Yu、Akagawa Kengo、Mutai Toshiki、Yoshikawa Isao、Kudo Kazuaki
    • Journal Title

      Tetrahedron

      Volume: - Pages: 132146-132146

    • DOI

      10.1016/j.tet.2021.132146

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] A superelastochromic crystal2020

    • Author(s)
      Mutai Toshiki、Sasaki Toshiyuki、Sakamoto Shunichi、Yoshikawa Isao、Houjou Hirohiko、Takamizawa Satoshi
    • Journal Title

      Nature Communications

      Volume: 11 Issue: 1 Pages: 1824-1824

    • DOI

      10.1038/s41467-020-15663-5

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Improvement of the Cycle Property of Binder-Free LiCoO<sub>2</sub> Positive Electrode Film Deposited via the Pulsed Electrophoretic Deposition2019

    • Author(s)
      Miyazaki Hidetoshi、Mimaru Yu、Makinose Yuki、Tsuji Takeshi、Yamada Hirotoshi、Mutai Toshiki
    • Journal Title

      MATERIALS TRANSACTIONS

      Volume: 60 Issue: 12 Pages: 2576-2579

    • DOI

      10.2320/matertrans.MT-M2019112

    • NAID

      130007751040

    • ISSN
      1345-9678, 1347-5320
    • Year and Date
      2019-12-01
    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene2019

    • Author(s)
      Kono Luna、Nakagawa Yuma、Fujimoto Ayako、Nishimura Ryo、Hattori Yohei、Mutai Toshiki、Yasuda Nobuhiro、Koizumi Kenichi、Yokojima Satoshi、Nakamura Shinichiro、Uchida Kingo
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 15 Pages: 2204-2212

    • DOI

      10.3762/bjoc.15.217

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Photochromism of salicylideneanilines bearing super bulky substituents: Single-crystal UV-vis spectroscopic examination of bleaching under variable temperature and visible-light irradiation2019

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

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 385 Pages: 112096-112105

    • DOI

      10.1016/j.jphotochem.2019.112096

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Halogen-substituent effect on the spectroscopic properties of 2-phenyl-6-dimethylaminobenzothiazoles2019

    • Author(s)
      Misawa Rena、Matsuhashi Chihiro、Yamaji Minoru、Mutai Toshiki、Yoshikawa Isao、Houjou Hirohiko、Noguchi Keiichi、Maki Shojiro、Hirano Takashi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 26 Pages: 1702-1705

    • DOI

      10.1016/j.tetlet.2019.05.052

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機結晶の超弾性発光クロミズム2020

    • Author(s)
      務台 俊樹, 佐々木 俊之, 坂元 駿一, 吉川 功, 北條 博彦, 髙見澤 聡
    • Organizer
      2020光化学討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] メカノクロミック発光性結晶材料に対する定量的な機械刺激応答性解析2020

    • Author(s)
      伊藤 傑, 永井 彩香, 池谷 美菜子, 眞下 峻希, 関 朋宏, 伊藤 肇, 相良 剛光, 務台 俊樹, 大山 陽介, 中野 健
    • Organizer
      2020光化学討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] 結晶の集積構造変化(メカノクロミックの関与)について2020

    • Author(s)
      務台俊樹
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 1.Quantitative analysis of mechanical stimuli-responsiveness for mechanochromic luminophores2020

    • Author(s)
      Minako Ikeya, Takaki Mashimo, Tomohiro Seki, Hajime Ito, Yoshimitsu Sagara, Toshiki Mutai, Yousuke Ooyama, Ken Nakano
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 七員環型分子内水素結合を有するイミダゾピリジン誘導体の酸・塩基条件における光学特性2020

    • Author(s)
      鈴木 陸人, 務台 俊樹, 真崎 康博
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Development of Polymorph-Dependent Luminescente Crystals Based on the Excited-State Intramolecular Proton Transfer2019

    • Author(s)
      Toshiki Mutai
    • Organizer
      The 2nd International Symposium on Soft Crystals (2ndISSC)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 七員環型分子内水素結合を有するESIPT発光分子の固体発光と置換基効果2019

    • Author(s)
      鈴木 陸人, 務台 俊樹, 真崎 康博
    • Organizer
      第13回有機π電子系シンポジウム
    • Related Report
      2019 Research-status 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結晶構造と発光特性2019

    • Author(s)
      務台 俊樹, 鈴木 陸人, 吉川 功, 北條 博彦, 工藤 一秋
    • Organizer
      第28回有機結晶シンポジウム
    • Related Report
      2019 Research-status 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結晶構造とESIPT発光特性2019

    • Author(s)
      務台 俊樹, 鈴木 陸人, 吉川 功, 北條 博彦, 工藤 一秋
    • Organizer
      2019光化学討論会
    • Related Report
      2019 Research-status Report
  • [Book] Advances in Organic Crystal Chemistry, Comprehensive Reviews 20202020

    • Author(s)
      Ed. by Masami Sakamoto and Hidehiro Uekusa
    • Total Pages
      538
    • Publisher
      Springer Nature Singapore Pte Ltd.
    • ISBN
      9789811550843
    • Related Report
      2020 Research-status Report
  • [Remarks] 有機超弾性結晶の発光クロミズム ~小さな力で分子配列を変換し発光色の可逆制御を有機結晶で実現~

    • URL

      https://www.iis.u-tokyo.ac.jp/ja/news/3285/

    • Related Report
      2020 Research-status Report

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Published: 2019-04-18   Modified: 2023-01-30  

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