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Investigation for fluorenylidene-acridane that shows ground state mechanochromism

Research Project

Project/Area Number 17K19116
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Research Field Organic chemistry and related fields
Research InstitutionThe University of Tokyo

Principal Investigator

Matsuo Yutaka  東京大学, 大学院工学系研究科(工学部), 特任教授 (00334243)

Project Period (FY) 2017-06-30 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2018: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2017: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywordsアクリダン / アクリジニウム / クロミズム / メカノクロミズム / 有機半導体 / 色素 / 刺激応答性材料 / フルオレン / 感圧材料 / 配座変化 / コンフォマー / フルオレニリデン / 分子性固体
Outline of Final Research Achievements

We synthesized Fluorenylidene-acridanes that changes their absorption colors by mechanical stimuli. We elucidated that the mechanism of this appearance change is based on conformational change of the molecules, which can be controlled by morphological change in the solid. We also achieved X-ray single crystal structures determination of both folded and twisted conformers. This revealed that absorption color change was governed by switching charge transfer absorption.

Academic Significance and Societal Importance of the Research Achievements

機械的刺激や圧力により見た目の色が大きく変わる材料は世の中にあまりなく,押すと黄色から深い緑色に変わる分子を新たに創製した.感圧紙や歯科医で用いられる咬合紙では圧力があるとカプセルに封入された色素が外に出て色がつくが,この分子では分子の形状が変化して分子のみで大きく色が変わる.そしてこの時,電気の流れやすさも変わる.このような特異な性質を利用して,圧力センサーなどへの応用が期待される.

Report

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

    (12 results)

All 2019 2018 Other

All Int'l Joint Research (2 results) Journal Article (4 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 4 results,  Open Access: 1 results) Presentation (4 results) (of which Int'l Joint Research: 1 results) Remarks (2 results)

  • [Int'l Joint Research] 中国科学技術大学/中国科学院化学研究所(中国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] USTC/Northeast Normal University(中国)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Reduced Knoevenagel Reaction of Acetetracenylene-1,2-dione with Acceptor Units for Luminescent Tetracene Derivatives2019

    • Author(s)
      Matsuo Yutaka、Yu Chu-Guo、Nakagawa Takafumi、Okada Hiroshi、Ueno Hiroshi、Sun Tian-Ge、Zhong Yu-Wu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 4 Pages: 2339-2345

    • DOI

      10.1021/acs.joc.8b03083

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Mechanochromism, Twisted/Folded Structures Determination, and Derivatization of N-Phenyl Fluorenylidene-Acridane2019

    • Author(s)
      Matsuo Yutaka、Wang Ya、Ueno Hiroshi、Nakagawa Takafumi、Okada Hiroshi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 印刷中 Issue: 26 Pages: 8762-8767

    • DOI

      10.1002/anie.201902636

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Fluorenylidene-Acridane That Becomes Dark in Color upon Grinding _ Ground State Mechanochromism by Conformational Change2018

    • Author(s)
      Tsuyoshi Suzuki, Hiroshi Okada, Takafumi Nakagawa, Kazuki Komatsu, Chikako Fujimoto, Hiroyuki Kagi, Yutaka Matsuo
    • Journal Title

      Chem. Sci.

      Volume: 9 Issue: 2 Pages: 475-482

    • DOI

      10.1039/c7sc03567e

    • NAID

      120006708961

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Helically-Twisted Ladder Based on 9,90-Bifluorenylidene: Synthesis, Characterization, and Charge Transport Properties2018

    • Author(s)
      Jinjia Xu, Atsuro Takai, Alisa Bannaron, Takafumi Nakagawa, Yutaka Matsuo, Manabu Sugimoto, Yoshitaka Matsushita, Masayuki Takeuchi
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 4 Pages: 780-784

    • DOI

      10.1039/c7qm00583k

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis, Structures, and Ground State Mechanochromism of N-Phenyl Substituted Fluorenylidene-Acridane2018

    • Author(s)
      Yutaka Matsuo, Ya Wang
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フルオレニリデン-アクリダンの合成,構造と基底状態メカノクロミズム2018

    • Author(s)
      松尾 豊,王 亜,中川 貴文,岡田洋史,上野 裕
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] N-フェニル置換フルオレニリデン-アクリダンの合成,構造と基底状態メカノクロミズム2018

    • Author(s)
      松尾 豊,王 亜,上野 裕,中川 貴文,岡田洋史
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Fluorenylidene-acridane, A Molecule That Becomes Dark Color When Its Crystals Are Ground2018

    • Author(s)
      Yutaka Matsuo, Tsuyoshi Suzuki, Ya Wang, Hiroshi Okada, Takafumi Nakagawa
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA 2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Remarks] 力を加えると大きく色が変わる分子を発見 ~新規の機能性材料への応用に期待~

    • URL

      https://www.t.u-tokyo.ac.jp/foe/press/setnws_201711161635263335245369.html

    • Related Report
      2018 Annual Research Report
  • [Remarks] Matsuo Group at USTC and Tokyo

    • URL

      http://www.matsuo-lab.net

    • Related Report
      2017 Research-status Report

URL: 

Published: 2017-07-21   Modified: 2020-03-30  

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