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2021 Fiscal Year Annual Research Report

Construction of chiral macromolecular structure through controlled chemical bond rotation by circularly polarized light irradiation

Research Project

Project/Area Number 19H02759
Research InstitutionHokkaido University

Principal Investigator

中野 環  北海道大学, 触媒科学研究所, 教授 (40227856)

Co-Investigator(Kenkyū-buntansha) 宋 志毅  北海道大学, 触媒科学研究所, 准教授 (80600981)
Project Period (FY) 2019-04-01 – 2022-03-31
Keywords円偏光 / らせん / ねじれ / キラル増幅 / 円偏光二色性スペクトル
Outline of Annual Research Achievements

円偏光を用いた直鎖高分子への不斉誘起の研究対象を、これまで検討してきたフルオレン-2,7-ジイル型単位およびベンゼン-1,4-ジイル型単位を基礎とする折れ曲がりの無い高分子から、折れ曲がり構造を導入した高分子へと拡張した。加えて、これまでの円偏光法の主な適用対象が規則的な化学構造(モノマー単位配列)を有する高分子であったの対し、ランダム共重合により得られる不規則な化学構造を有するに対して適用した。折れ曲がり構造を有する高分子として数種のポリベンゼン-1,3-ジイル型単位を有するポリベンゼン類を合成し、円偏光法による光学活性化を検討したところ、効率よくキラル構造を構築できることが明らかになった。また、数種のベンゼン-1,4-ジイル型モノマーのランダム共重合により得られた高分子が、円偏光照射により従来検討した他の高分子より相当に高い効率で光学活性化することを見出した。本研究ではこれまでに、円偏光法を効率的に利用するためには(a)鎖間の相互作用の強い規則的な固体構造、および、(b)固体中で10msec程度の時間スケールで内部回転する高分子構造、の2つの要因が重要であることを明らかにしており、これらの必ずしも両立しやすくはない2つの特徴が、折れ曲がり構造の導入およびモノマー単位のランダム配列により実現されたものと考えられる。これらの構造の導入により分子間のパッキングが密になり過ぎず内部回転の時間スケールが最適に調整される可能性が高い。

Research Progress Status

令和3年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

令和3年度が最終年度であるため、記入しない。

  • Research Products

    (25 results)

All 2022 2021 Other

All Int'l Joint Research (1 results) Journal Article (11 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 10 results,  Open Access: 2 results) Presentation (13 results) (of which Int'l Joint Research: 6 results,  Invited: 5 results)

  • [Int'l Joint Research] カタンザロ大学(イタリア)

    • Country Name
      ITALY
    • Counterpart Institution
      カタンザロ大学
  • [Journal Article] Synthesis of porous polymers by means of Michael addition reaction of multifunctional acetoacetate and poly(ethylene glycol) diacrylate2022

    • Author(s)
      Naga Naofumi、Satoh Mitsusuke、Magara Tomoyuki、Ahmed Kumkum、Nakano Tamaki
    • Journal Title

      European Polymer Journal

      Volume: 162 Pages: 110901~110901

    • DOI

      10.1016/j.eurpolymj.2021.110901

    • Peer Reviewed
  • [Journal Article] Aggregation-induced chirality amplification of optically active fluorescent polyurethane and a cyclic dimer in the ground and excited states2022

    • Author(s)
      Song Zhiyi、Sato Hiroyasu、Pietropaolo Adriana、Wang Qingyu、Shimoda Shuhei、Dai Heshuang、Imai Yoshitane、Toda Hayato、Harada Takunori、Shichibu Yukatsu、Konishi Katsuaki、Bando Masayoshi、Naga Naofumi、Nakano Tamaki
    • Journal Title

      Chemical Communications

      Volume: 58 Pages: 1029~1032

    • DOI

      10.1039/D1CC05633F

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dielectric Permittivity, AC Electrical Conductivity and Conduction Mechanism of High Crosslinked-Vinyl Polymers and Their Pd(OAc)2 Composites2021

    • Author(s)
      Elbayoumy Elsayed、El-Ghamaz Nasser A.、Mohamed Farid Sh.、Diab Mostafa A.、Nakano Tamaki
    • Journal Title

      Polymers

      Volume: 13 Pages: 3005~3005

    • DOI

      10.3390/polym13173005

    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Pd Nanoparticles-Loaded Vinyl Polymer Gels: Preparation, Structure and Catalysis2021

    • Author(s)
      Elbayoumy Elsayed、Wang Yuting、Rahman Jamil、Trombini Claudio、Bando Masayoshi、Song Zhiyi、Diab Mostafa A.、Mohamed Farid S.、Naga Naofumi、Nakano Tamaki
    • Journal Title

      Catalysts

      Volume: 11 Pages: 137~137

    • DOI

      10.3390/catal11010137

    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of gels by means of Michael addition reaction of multi‐functional acetoacetate and diacrylate compounds and their application to ionic conductive gels2021

    • Author(s)
      Naga Naofumi、Satoh Mitsusuke、Magara Tomoyuki、Ahmed Kumkum、Nakano Tamaki
    • Journal Title

      Journal of Polymer Science

      Volume: 59 Pages: 2129~2139

    • DOI

      10.1002/pol.20210388

    • Peer Reviewed
  • [Journal Article] Synthesis of network polymers by photo-initiated thiol-ene reaction between multi-functional thiol and poly(ethylene glycol) diacrylate2021

    • Author(s)
      Naga Naofumi、Yamada Kohei、Moriyama Kazumasa、Kudoh Shuntaro、Nagami Yosuke、Nageh Hassan、Nakano Tamaki
    • Journal Title

      Polymer Bulletin

      Volume: 79 Pages: 2411~2427

    • DOI

      10.1007/s00289-021-03643-8

    • Peer Reviewed
  • [Journal Article] Photo racemization of 2,2′‐dihydroxy‐1,1′‐binaphthyl derivatives2021

    • Author(s)
      Wang Qingyu、Pietropaolo Adriana、Fortino Mariagrazia、Song Zhiyi、Bando Masayoshi、Naga Naofumi、Nakano Tamaki
    • Journal Title

      Chirality

      Volume: 34 Pages: 317~324

    • DOI

      10.1002/chir.23400

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Triad Fluorenone Derivative Bearing Two Imidazole Groups That Switches between Three States by Base and Acid Stimuli2021

    • Author(s)
      Wang Yuting、Maity Nabin、Zhao Liming、Kr?mer Maximilian、Hasegawa Jun-ya、Shichibu Yukatsu、Konishi Katsuaki、Wang Xiaoyuan、Song Zhiyi、Bando Masayoshi、Nakano Tamaki
    • Journal Title

      Chemistry Letters

      Volume: 50 Pages: 1363~1367

    • DOI

      10.1246/cl.210112

    • Peer Reviewed
  • [Journal Article] Optically active covalent organic frameworks and hyperbranched polymers with chirality induced by circularly polarized light2021

    • Author(s)
      Wang Yuting、Yazawa Koji、Wang Qingyu、Harada Takunori、Shimoda Shuhei、Song Zhiyi、Bando Masayoshi、Naga Naofumi、Nakano Tamaki
    • Journal Title

      Chemical Communications

      Volume: 57 Pages: 7681~7684

    • DOI

      10.1039/d1cc02671b

    • Peer Reviewed
  • [Journal Article] Blue circularly polarized luminescent amorphous molecules with single-handed propeller chirality induced by circularly polarized light irradiation2021

    • Author(s)
      Zhang Zhaoming、Harada Takunori、Pietropaolo Adriana、Wang Yuting、Wang Yue、Hu Xiao、He Xuehan、Chen Hui、Song Zhiyi、Bando Masayoshi、Nakano Tamaki
    • Journal Title

      Chemical Communications

      Volume: 57 Pages: 1794~1797

    • DOI

      10.1039/d0cc07898k

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] らせん・ねじれ構造を有する高分子・超分子2021

    • Author(s)
      中野 環
    • Journal Title

      高分子

      Volume: 70 Pages: 613~617

  • [Presentation] Circularly Polarized Light (CPL)-driven Preparation of Chiral Polymers and Molecules That Emit CPL2022

    • Author(s)
      Tamaki Nakano
    • Organizer
      ICCC-2022 (International CREST-CPL Conference 2022 in Awaji, JAPAN)
    • Int'l Joint Research / Invited
  • [Presentation] Construction of Chiral Conformation of Polymers and Small Molecules Using Circularly Polarized Light2022

    • Author(s)
      Tamaki Nakano
    • Organizer
      Fourth JSPS Alumni Association in Australia Fourth Annual Symposium: CATALYSING AUSTRALIA-JAPAN SCIENCE AND INNOVATION
    • Int'l Joint Research / Invited
  • [Presentation] Understanding Polymer Chirality2021

    • Author(s)
      Tamaki Nakano
    • Organizer
      The 48th World Polymer Congress IUPAC-MACRO2020+
    • Int'l Joint Research / Invited
  • [Presentation] ポリ(フェナントレン‐9,10‐ジイル)の合成と構造2021

    • Author(s)
      坂東正佳・宋志毅・中野環
    • Organizer
      第70回高分子学会年次大会
  • [Presentation] Synthesis and Properties of Hyperbranched and Linear, Optically Active Poly(fluorenevinylene) Derivatives2021

    • Author(s)
      Pengfei Wu, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    • Organizer
      第70回高分子学会年次大会
  • [Presentation] Synthesis of Poly(benzene-1,4-diyl) Derivatives Bearing Bulky Side-chain Groups2021

    • Author(s)
      ingyu Wang,, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    • Organizer
      第70回高分子学会年次大会
  • [Presentation] フルオレン残基を主鎖中に有する光学活性ポリウレタンの合成と性質2021

    • Author(s)
      宋 志毅 ・ 戴 河双 ・板東正佳 ・中野 環
    • Organizer
      第70回高分子学会年次大会
  • [Presentation] Synthesis and Structure of Optically Active Poly(benzene-1,4-diyl) Derivatives Bearing Bulky Side-chain Groups2021

    • Author(s)
      Qingyu Wang, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    • Organizer
      第70回高分子討論会
  • [Presentation] Synthesis and Structural Isomerization of Hyperbranced Optically Active Poly(fluorenevinylene) Derivatives2021

    • Author(s)
      Pengfei Wu, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    • Organizer
      第70回高分子討論会
  • [Presentation] フルオレン残基を有する発光性キラルポリウレタンの合成と性質2021

    • Author(s)
      宋 志毅 ・ 戴 河双 ・板東正佳 ・中野 環
    • Organizer
      第70回高分子討論会
  • [Presentation] Synthesis of Optically Active Polymer Systems Using Circularly Polarized Light (CPL) as the Source of Chirality2021

    • Author(s)
      Tamaki Nakano, Yuting Wang, Zhiyi Song, and Masayoshi Bando
    • Organizer
      Pacifichem 2021 #274 Chirality of Polymers and Supramolecules
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and chirality of hyperbranched poly(benzene-1,4-diyl) derivatives2021

    • Author(s)
      Yuting Wang, Qingyu Wang, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    • Organizer
      Pacifichem 2021 #274 Chirality of Polymers and Supramolecules
    • Int'l Joint Research
  • [Presentation] Optically Active Polymers and Polymer-based Small-Molecular Systems for CPL Emission2021

    • Author(s)
      Tamaki Nakano
    • Organizer
      Pacifichem 2021 #307 Recent Progress in Circularly Polarized Luminescence (CPL) and Related Phenomena: Synthesis and Photophysics
    • Int'l Joint Research / Invited

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Published: 2022-12-28  

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