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Development of Cyclophane-based Supramolecular Mechanophores and the Applications for Polymeric Materials

Research Project

Project/Area Number 18H02024
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 35020:Polymer materials-related
Research InstitutionTokyo Institute of Technology (2020-2021)
Hokkaido University (2018-2019)

Principal Investigator

Sagara Yoshimitsu  東京工業大学, 物質理工学院, 准教授 (60767292)

Co-Investigator(Kenkyū-buntansha) キム ユナ  北海道大学, 電子科学研究所, 准教授 (00648131)
Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Fiscal Year 2021: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2020: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2019: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2018: ¥10,530,000 (Direct Cost: ¥8,100,000、Indirect Cost: ¥2,430,000)
Keywords超分子メカノフォア / シクロファン / 蛍光 / 機械的刺激応答性発光材料 / 電荷移動錯体 / メカノフォア / 超分子 / 刺激応答性発光材料 / エラストマー / ポリウレタン / 超分子化学
Outline of Final Research Achievements

Recently, mechanophores that change absorption and fluorescence properties responding to mechanical stimuli have been extensively studied. In this study, we developed a supramolecular mechanophore based on cyclophane. When cyclophane-based supramolecular mechanophores with one fluorophore and one quencher are introduced into polyurethane, the film obtained through solvent casting shows an orange fluorescence color derived from the charge-transfer complex between the fluorophore and quencher. When the film is stretched, the fluorophore and quencher are spatially separated and blue fluorescence from the fluorophore is observed. This ratiometric fluorescence color change is instantly reversible.

Academic Significance and Societal Importance of the Research Achievements

我々がこれまでに報告してきたロタキサンをモチーフとした超分子だけでなく、単純な環状分子であるシクロファンを用いても超分子メカノフォアを構築できることが明らかになった。本成果により超分子メカノフォアの分子設計の自由さが改めて示されたと言え、分野の進展・深化が期待できる。また、これまでに報告されてきたメカノフォアの中で電荷移動錯体を積極活用したメカノフォアはほぼ存在せず、新規性が高いと言える。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (25 results)

All 2022 2021 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (7 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 7 results,  Open Access: 3 results) Presentation (13 results) (of which Int'l Joint Research: 5 results,  Invited: 5 results) Remarks (2 results)

  • [Int'l Joint Research] Adolphe Merkle Institute(スイス)

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] Adolphe Merkle Institute(スイス)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Adolphe Merkle Institute(スイス)

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Crystal structure of a 1,6-bis(phenylethynyl)pyrene-based cyclophane that exhibits mechanochromic luminescence2021

    • Author(s)
      Shimizu Shohei、Thazhathethil Shakkeeb、Takahashi Kiyonori、Nakamura Takayoshi、Sagara Yoshimitsu
    • Journal Title

      Molecular Systems Design & Engineering

      Volume: 6 Issue: 12 Pages: 1039-1046

    • DOI

      10.1039/d1me00131k

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rotaxane-Based Dual Function Mechanophores Exhibiting Reversible and Irreversible Responses2021

    • Author(s)
      Muramatsu Tatsuya、Okado Yuji、Traeger Hanna、Schrettl Stephen、Tamaoki Nobuyuki、Weder Christoph、Sagara Yoshimitsu
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 26 Pages: 9884-9892

    • DOI

      10.1021/jacs.1c03790

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Mechanically Responsive Luminescent Polymers Based on Supramolecular Cyclophane Mechanophores2021

    • Author(s)
      Sagara Yoshimitsu、Traeger Hanna、Li Jie、Okado Yuji、Schrettl Stephen、Tamaoki Nobuyuki、Weder Christoph
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 14 Pages: 5519-5525

    • DOI

      10.1021/jacs.1c01328

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Two-step mechanoresponsive luminescence and mechanical stimuli-induced release of small molecules exhibited by a luminescent cyclophane2021

    • Author(s)
      Sagara Yoshimitsu、Takahashi Kiyonori、Seki Atsushi、Muramatsu Tatsuya、Nakamura Takayoshi、Tamaoki Nobuyuki
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 9 Issue: 5 Pages: 1671-1677

    • DOI

      10.1039/d0tc04853d

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Crystal structure and thermoresponsive luminescence of a 9,10-bis(phenylethynyl)anthracene-based cyclophane2020

    • Author(s)
      Yoshimitsu Sagara, Kiyonori Takahashi,Takayoshi Nakamura, Nobuyuki Tamaoki
    • Journal Title

      Molecular Systems Design & Engineering

      Volume: 1 Issue: 1 Pages: 205-211

    • DOI

      10.1039/c9me00105k

    • NAID

      120006950868

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A 1,6-Diphenylpyrene-Based, Photoluminescent Cyclophane Showing a Nematic Liquid-Crystalline Phase at Room Temperature2019

    • Author(s)
      Sagara Yoshimitsu、Muramatsu Tatsuya、Tamaoki Nobuyuki
    • Journal Title

      Crystals

      Volume: 9 Issue: 2 Pages: 92-92

    • DOI

      10.3390/cryst9020092

    • NAID

      120006711963

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Linearly polarized photoluminescence from an asymmetric cyclophane showing thermo- and mechanoresponsive luminescence2018

    • Author(s)
      Sagara Yoshimitsu、Seki Atsushi、Kim Yuna、Tamaoki Nobuyuki
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 6 Issue: 31 Pages: 8453-8459

    • DOI

      10.1039/c8tc02919a

    • NAID

      120006713296

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] A Cyclophane-based Supramolecular Mechanophore that Shows Ratiometric Change in Emission Between Monomer and Exciplex2022

    • Author(s)
      Shakkeeb Thazhathethil, Nobuyuki Tamaoki, Yoshimitsu Sagara
    • Organizer
      日本化学会第102春季年会(2022)
    • Related Report
      2021 Annual Research Report
  • [Presentation] Supramolecular Mechanophores Working at Single Molecular Level2022

    • Author(s)
      Yoshimitsu Sagara
    • Organizer
      The 2nd International Workshop on Molecular Engine
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 1分子レベルで力を可視化する 超分子メカノフォア2021

    • Author(s)
      相良剛光
    • Organizer
      日本学術振興会 分子系の複合電子機能第181委員会 第36回研究会「有機材料の力学応答」
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 1分子レベルで機能する超分子メカノフォア2021

    • Author(s)
      相良剛光
    • Organizer
      第42回光化学若手の会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Supramolecular Mechanophores Working at Molecular Level2021

    • Author(s)
      Yoshimitsu Sagara
    • Organizer
      2021 Taiwan-Japan Bilateral Polymer Symposium
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 蛍光特性変化を示す超分子メカノフォア2021

    • Author(s)
      相良剛光
    • Organizer
      第30回ポリマー材料フォーラム
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Supramolecular mechanophores that work at single molecular level2021

    • Author(s)
      Yoshimitsu Sagara
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of a Cyclophane-based Supramolecular Mechanophore Forming Exciplex2021

    • Author(s)
      Shakkeeb Thazhathethil, Nobuyuki Tamaoki, Yoshimitsu Sagara
    • Organizer
      the 22nd RIES-HOKUDAI International Symposium
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A cyclophane-based supramolecular mechanophore changing the ratio of exciplex to monomer emission intensities2021

    • Author(s)
      THAZHATHETHIL Shakkeeb・SAGARA Yoshimitsu
    • Organizer
      第11回CSJ化学フェスタ2021
    • Related Report
      2021 Annual Research Report
  • [Presentation] レシオメトリックな蛍光特性変化を示すシクロファン型超分子メカノフォア.2021

    • Author(s)
      サザセティル シャキーブ・相良 剛光
    • Organizer
      第30回ポリマー材料フォーラム
    • Related Report
      2021 Annual Research Report
  • [Presentation] Development of A Cyclophane-based Supramolecular Mechanophore Utilizing Charge-transfer Interaction2021

    • Author(s)
      Shakkeeb Thazhathethil, Yoshimitsu Sagara
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 機械的刺激に応答して発光特性が 変化する有機機能性材料2019

    • Author(s)
      相良剛光
    • Organizer
      生命理工学院セミナー(東工大)
    • Related Report
      2018 Annual Research Report
  • [Presentation] 環状構造を利用した 外部刺激に応答する有機発光材料2018

    • Author(s)
      相良剛光
    • Organizer
      北海道高分子若手研究会
    • Related Report
      2018 Annual Research Report
  • [Remarks] 相良研究室のページ

    • URL

      https://sagara.mat.mac.titech.ac.jp/

    • Related Report
      2021 Annual Research Report
  • [Remarks] 相良剛光の個人ページ

    • URL

      https://ysagara-mechano.wixsite.com/mysite

    • Related Report
      2019 Annual Research Report

URL: 

Published: 2018-04-23   Modified: 2023-01-30  

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