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Synthesis of hetero[3]rotaxanes with noble molecular shuttling directed toward higher-order molecular machines

Research Project

Project/Area Number 17K14446
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Masai Hiroshi  東京大学, 大学院総合文化研究科, 特任研究員 (70793149)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2017: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywordsロタキサン / サーモクロミック / シャトリング / 超分子 / 超分子化学 / 分子機械
Outline of Final Research Achievements

In this work, a thermochromic response was developed by using a [3]rotaxane structure bearing an emission moiety. The two cyclic molecules covered the luminescent chromophore. Under a heat, the cyclic molecules thermally shuttled, so that the emission behavior of the [3]rotaxane was changed, where the chromophore was exposed to the surrounding other molecules. The luminescent changes could be repeatedly conducted under heating-cooling cycles.

Academic Significance and Societal Importance of the Research Achievements

分子機械の重要なモチーフであるロタキサン構造において、熱シャトリングは比較的初期から報告されていたものの、停留点(ステーション)の制御が困難であることから、材料の物性を向上させる設計としてはほとんど用いられてこなかった。対して本研究は超分子構造の熱シャトリングを用いて、シャトリングを起こさない材料よりも鋭敏な熱応答性を発現したことから、センサ材料における新しい設計指針を示したと言える。

Report

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

    (16 results)

All 2019 2018 2017

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 7 results) Presentation (7 results) (of which Int'l Joint Research: 1 results) Book (1 results)

  • [Journal Article] Synthetic Methodology for Structurally defined and Unidirectional Insulated Molecular Wires via Iterative Intramolecular Slippage2019

    • Author(s)
      Sheng-Ying Chou, Hiroshi Masai, Susumu Tsuda, Jun Terao
    • Journal Title

      Chem. Asian J.

      Volume: 印刷中 Issue: 10 Pages: 1667-1671

    • DOI

      10.1002/asia.201801706

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Platinum-Acetylide Crosslinkers for Facile Preparation of Phosphorescent Commodity Polymer Networks with Defect-Free Chromophores2019

    • Author(s)
      Go M. Russell, Hiroshi Masai
    • Journal Title

      Mater. Let.

      Volume: 247 Pages: 182-184

    • DOI

      10.1016/j.matlet.2019.03.123

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Acid-Responsiveness of an Insulated p-Conjugated Polymer containing Spiropyrans in its Backbone2019

    • Author(s)
      Hiromichi V. Miyagishi, Takashi Tamaki, Hiroshi Masai, Jun Terao
    • Journal Title

      Molecules

      Volume: 24 Issue: 7 Pages: 1301-1301

    • DOI

      10.3390/molecules24071301

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Reversible and Stable Redox Behavior of a Pt(II) Bis(dithiobenzoate)-type Complex Attributed to Rotaxane-based Stabilization2018

    • Author(s)
      Ryosuke Harada, Takuro Hosomi, Hiroshi Masai, Jun Terao
    • Journal Title

      Tetrahedron Lett.

      Volume: 59 Issue: 30 Pages: 2930-2933

    • DOI

      10.1016/j.tetlet.2018.06.034

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Kinetic Stabilization of a Ni(II) Bis(dithiobenzoate)-type Complex Achieved Using Three-dimensional Insulation by a [1]Rotaxane Structure2018

    • Author(s)
      Takuro Hosomi, Ryosuke Harada, Hiroshi Masai, Tetsuaki Fujihara, Yasushi Tsuji, Jun Terao
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 20 Pages: 2487-2490

    • DOI

      10.1039/c8cc00351c

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Regio- and Stereoselective Synthesis of Triarylalkene-Capped Rotaxanes via Palladium-Catalyzed Tandem Sonogashira/Hydroaryl Reaction of Terminal Alkynes2017

    • Author(s)
      Masai Hiroshi、Matsuda Wakana、Fujihara Tetsuaki、Tsuji Yasushi、Terao Jun
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 10 Pages: 5449-5455

    • DOI

      10.1021/acs.joc.7b00442

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins2017

    • Author(s)
      Masai Hiroshi、Fujihara Tetsuaki、Tsuji Yasushi、Terao Jun
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 60 Pages: 15073-15079

    • DOI

      10.1002/chem.201701428

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stimuli-responsive functionalized insulated conjugated polymers2017

    • Author(s)
      Masai Hiroshi、Terao Jun
    • Journal Title

      Polymer Journal

      Volume: 49 Issue: 12 Pages: 805-814

    • DOI

      10.1038/pj.2017.57

    • NAID

      40021391987

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 被覆型白金アセチリドポリマーを用いた塩化水素ガスの固体発光センサの開発2018

    • Author(s)
      正井 宏、横山琢也、寺尾 潤
    • Organizer
      第35回シクロデキストリンシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 共役ジチオカルボン酸を用いた有機・無機ハイブリッド材料における被覆効果2018

    • Author(s)
      原田涼佑・細見拓郎・正井宏・寺尾潤
    • Organizer
      ナノスケール分子デバイス「第七回若手セミナー」
    • Related Report
      2017 Research-status Report
  • [Presentation] 金属ビスジチオベンゾエート錯体の合成およびその酸化還元挙動に対する環状被覆効果2018

    • Author(s)
      原田涼佑・細見拓郎・正井宏・寺尾潤
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 被覆型共役メタロポリマーを用いた燐光ガスセンサ材料の開発2017

    • Author(s)
      横山琢矢・正井宏・寺尾潤・藤原哲晶・辻康之
    • Organizer
      第8回サブウェイセミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] メチル化シクロデキストリンを用いた被覆による不安定錯体の合成と速度論的安定化2017

    • Author(s)
      原田涼佑・細見拓郎・正井宏・藤原哲晶・辻康之・寺尾潤
    • Organizer
      第34回シクロデキストリンシンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 被覆型共役メタロワイヤを用いた燐光ガスセンサ材料の開発2017

    • Author(s)
      横山琢矢・正井宏・寺尾潤・藤原哲晶・辻康之
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Functionalized Insulated Molecular Wires2017

    • Author(s)
      Hiroshi Masai and Jun Terao
    • Organizer
      Single-Molecule Science and Technology
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Book] 分子アーキテクトニクス Chapter 7 機能性分子ワイヤ2018

    • Author(s)
      寺尾潤 正井宏
    • Publisher
      化学同人
    • Related Report
      2018 Annual Research Report

URL: 

Published: 2017-04-28   Modified: 2020-03-30  

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