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Synthesis of polycatenanes using equilibrium reactions with cyclic structure and supramolecular interactions

Research Project

Project/Area Number 21K18996
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 35:Polymers, organic materials, and related fields
Research InstitutionChiba University (2022)
Tokyo Institute of Technology (2021)

Principal Investigator

Aoki Daisuke  千葉大学, 大学院工学研究院, 准教授 (80736950)

Project Period (FY) 2021-07-09 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2022: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2021: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Keywordsカテナン / ロタキサン / ポリカテナン / 環状 / ラジカル / 動的共有結合 / 超分子 / 空間連結 / エントロピー / ジスルフィド / トポロジー
Outline of Research at the Start

熱によってその動的特性のon-offを制御可能なビス(2,2,6,6-テトラメチルピペリジン-1-イル)ジスルフィドを分子骨格内に有する環状化合物は、末端を有さないため濃厚条件で加熱すると環状高分子となり、希釈条件下で加熱すると元の環状化合物へと戻る。すなわち、末端のない新しい平衡系(環状化合物-環状高分子の平衡)を生み出す。本研究課題では、この環状分子のみ与える選択的環化反応(環状高分子から環状化合物への反応)と超分子的な相互作用を組み合わせることで、従来合成することが困難であったポリカテナンを合成する手法の確立を目指す。

Outline of Final Research Achievements

In this study, we established a selective cyclization reaction using a dynamic covalent bond that generates a stable radical as an intermediate, and by combining it with supramolecular interactions, we tried a method for easily and precisely synthesizing polycatenanes. Although we were not able to selectively synthesize polycatenane as originally planned, we succeeded in synthesizing [3]catenane by a relatively simple method. In the future, we aim to synthesize polycatenanes by designing optimal templates and chemical structures that facilitate the formation of supramolecular complexes. Through this research project, we were able to obtain several important results that will serve as the basis for polycatenan synthesis.

Academic Significance and Societal Importance of the Research Achievements

ポリカテナンは、高い伸張性や強靭性といった空間連結に由来する特異的な機能・物性を発現することが期待されている。すなわち、「安価」で「軽い」高分子材料の利点を生かしつつ、金属やセラミックスにも劣らぬ機能や強靭性をもつ高分子材料を創出し、材料化学が直面している薄膜化、軽量化の課題解決に対して解決策を打ち出すことができる。本研究で提案する合成手法は、斬新且つユニークな手法であり、高分子・超分子化学の発展に大きく資するものと期待している。

Report

(3 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • Research Products

    (13 results)

All 2022 2021

All Journal Article (3 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 3 results) Presentation (10 results) (of which Int'l Joint Research: 6 results)

  • [Journal Article] Mechanochromic Cyclodextrins2022

    • Author(s)
      Y. Sugita, D. Aoki, M. Tokita, H. Otsuka
    • Journal Title

      Chem. Commun.

      Volume: 58 Issue: 18 Pages: 3067-3070

    • DOI

      10.1039/d2cc00363e

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isolation of hetero-telechelic polyethylene glycol with groups of different reactivity at the chain ends2022

    • Author(s)
      Sato Tatsuki、Takashima Rikito、Aoki Daisuke、Otsuka Hideyuki
    • Journal Title

      Polymer Journal

      Volume: 54 Issue: 11 Pages: 1321-1329

    • DOI

      10.1038/s41428-022-00676-2

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthetic Strategy for Mechanically Interlocked Cyclic Polymers via the Ring-Expansion Polymerization of Macrocycles with a Bis(hindered amino)disulfide Linker2021

    • Author(s)
      Takashima Rikito、Aoki Daisuke、Otsuka Hideyuki
    • Journal Title

      Macromolecules

      Volume: 54 Issue: 17 Pages: 8154-8163

    • DOI

      10.1021/acs.macromol.1c01067

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Presentation] Formation of Macrocycles via Exchange Reactions of Bis(hindered amino)disulfide Linkages and Their Ring-expansion2022

    • Author(s)
      Rikito Takashima, Daisuke Aoki, Hideyuki Otsuka
    • Organizer
      IUMRS-ICYRAM2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Macrocycles via Exchange Reactions of Bis(hindered amino)disulfide Linkages and Their Polymerization Behavior2022

    • Author(s)
      Rikito Takashima, Daisuke Aoki, Hideyuki Otsuka
    • Organizer
      MACRO2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 末端に異なる反応性基を有するポリエチレングリコールの分離とその応用2022

    • Author(s)
      佐藤達紀、高嶋力任、青木大輔、大塚英幸
    • Organizer
      第71回高分子年次大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] マレイミドフェニルイソシアネートを用いた末端反応性高分子の合成とその応用2022

    • Author(s)
      佐藤達紀、高嶋力任、青木大輔、大塚英幸
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Isolation of Polyethylene Glycol with Terminal functional Groups of Different Reactivity t the Chain Ends2022

    • Author(s)
      Tatsuki Sato, Rikito Takashima, Daisuke Aoki, Hideyuki Otsuka
    • Organizer
      The 17th Pacific Polymer Conference
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A rational entry to cyclic polymers via rotaxane-based topological transformation2021

    • Author(s)
      Daisuke Aoki, Toshikazu Takata
    • Organizer
      ACS Spring 2022 National Meeting & Exposition
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthetic strategy for mechanically interlocked cyclic polymers using the exchange reaction of bis(hindered amino)disulfide2021

    • Author(s)
      Rikito Takashima, Daisuke Aoki, Hideyuki Otsuka
    • Organizer
      ACS Spring 2022 National Meeting & Exposition
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Thermally induced radical ring-expansion polymerization based on dynamic property of bis(hindered amino)disulfide-containing macrocycles2021

    • Author(s)
      Rikito Takashima, Daisuke Aoki, Hideyuki Otsuka
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] 嵩高いジスルフィドの結合交換反応を用いた環状高分子が空間的に連結した高分子の合成2021

    • Author(s)
      高嶋力任, 青木大輔, 大塚英幸
    • Organizer
      第70回高分子討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] 嵩高いジスルフィドの交換反応を利用した環状高分子が空間的に連結した高分子の合成2021

    • Author(s)
      高嶋力任, 青木大輔, 大塚英幸
    • Organizer
      第70回高分子年次大会
    • Related Report
      2021 Research-status Report

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Published: 2021-07-13   Modified: 2024-01-30  

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