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Development of chiral stationary phases capable of switchable enantioseparations based on helical polymers bearing biphenyl pendants

Research Project

Project/Area Number 24750100
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionKanazawa University

Principal Investigator

IKAI Tomoyuki  金沢大学, 物質化学系, 助教 (90402495)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords光学分割 / 機能性高分子 / ポリアセチレン / 不斉選択性 / 高次構造制御
Research Abstract

We have developed poly(biphenylylacetylene)s, which have a dynamic axial chirality and forms a preferred-handed helical conformation upon complexation with optically active compounds. The induced macromolecular helicity and axial chirality are memorized automatically and, further, are switchable in the solid state. This remarkable feature allowed us to develop a chiral packing material for the separation of enantiomers in which the elution order, or enantioselectivity, can be switched at will. In addition, we have synthesized poly(biphenylylacetylene)s bearing ester and carbamate groups as an interaction site and found that these polymers exhibited a high enantioselectivities against racemates, such as chiral metal complexes and axially chiral compounds.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (22 results)

All 2014 2013 2012 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (19 results) (of which Invited: 1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Switchable enantioseparation based on macromolecular memory of a helical polyacetylene in the solid state2014

    • Author(s)
      Shimomura, K.; Ikai, T.; Kanoh, S.; Yashima, E.; Maeda, K.
    • Journal Title

      Nat. Chem.

      Volume: 6 (5) Issue: 5 Pages: 429-434

    • DOI

      10.1038/nchem.1916

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Presentation] 様々な極性基を側鎖に導入したポリ(ビフェニルイルアセチレン)誘導体の合成と光学分割材料への応用2014

    • Author(s)
      井改知幸, 石立涼馬, 佐藤公、下村昴平, 前田勝浩, 加納重義, 八島栄次
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] 様々な極性基を側鎖に導入したポリ(ビフェニルイルアセチレン)誘導体の合成と光学分割材料への応用2014

    • Author(s)
      井改知幸・石立涼馬・佐藤公・下村昴平・前田勝浩・加納重義・八島栄次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] カルバメート基を側鎖に有するポリ(ビフェニルイルアセチレン)誘導体の合成と光学分割材料への応用2013

    • Author(s)
      佐藤公, 下村昂平, 井改知幸, 前田勝浩, 加納重義, 八島栄次
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢
    • Year and Date
      2013-09-12
    • Related Report
      2013 Final Research Report
  • [Presentation] Helicity Induction in Poly(biphenylylacetylene)s and Their Application to Chiral Stationary Phases for HPLC2013

    • Author(s)
      Tomoyuki Ikai, Kouhei Shimomura, Katsuhiro Maeda, Shigeyoshi Kanoh, Eiji Yashima
    • Organizer
      3^<rd> International Symposium on Chirality
    • Place of Presentation
      中国、哈爾濱
    • Year and Date
      2013-07-12
    • Related Report
      2013 Final Research Report
  • [Presentation] アルキルカルバメート基を側鎖に有するポリ(ビフェニルイルアセチレン)誘導体へのらせん誘起と光学分割材料への応用2013

    • Author(s)
      佐藤公, 下村昂平, 井改知幸, 前田勝浩, 加納重義, 八島栄次
    • Organizer
      第20回記念シンポジウムモレキュラー・キラリティー2013
    • Place of Presentation
      京都
    • Year and Date
      2013-05-10
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖に動的軸性キラルなビフェニル基を有するポリアセチレン誘導体へのらせん誘起とそのキラリティー識別への応用2013

    • Author(s)
      下村昂平, 前田勝浩, 井改知幸, 加納重義, 八島栄次
    • Organizer
      日本化学会第93春季年会(2013)
    • Place of Presentation
      草津
    • Year and Date
      2013-03-23
    • Related Report
      2013 Final Research Report
  • [Presentation] ポリ(ビフェニルイルアセチレン)誘導体を用いた不斉選択性の反転が可能なキラル固定相の開発2013

    • Author(s)
      井改知幸
    • Organizer
      第1回革新的キラルマテリアルの創製を目指したキラルナノテクノロジーの研究拠点形成シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2013-03-08
    • Related Report
      2013 Final Research Report
  • [Presentation] Helicity Induction in Poly(biphenylylacetylene)s and Their Application to Chiral Stationary Phases for HPLC2013

    • Author(s)
      Tomoyuki Ikai
    • Organizer
      3rd International Symposium on Chirality
    • Place of Presentation
      Harbin Engineering University
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] アルキルカルバメート基を側鎖に有するポリ(ビフェニルイルアセチレン)誘導体へのらせん誘起と光学分割材料への応用2013

    • Author(s)
      佐藤公・下村昴平・井改知幸・前田勝浩・加納重義・八島栄次
    • Organizer
      第20回記念シンポジウム モレキュラー・キラリティー2013
    • Place of Presentation
      京都大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体へのらせん誘起とその光学分割への応用2012

    • Author(s)
      下村昂平, 前田勝浩, 井改知幸, 加納重義, 八島栄次
    • Organizer
      第61回高分子学会北陸支部研究発表会
    • Place of Presentation
      福井
    • Year and Date
      2012-11-17
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体へのらせん誘起と記憶2012

    • Author(s)
      下村昂平, 前田勝浩, 井改知幸, 加納重義, 八島栄次
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2012-09-19
    • Related Report
      2013 Final Research Report
  • [Presentation] Helicity Control of Polyacetylene Derivative Bearing Biphenyl Pendants and Its Application to Chiral Stationary Phases for HPLC2012

    • Author(s)
      Tomoyuki Ikai, Kouhei Shimomura, Katsuhiro Maeda, Shigeyoshi Kanoh, Eiji Yashima
    • Organizer
      The 5^<th> Symposium on Molecular Chirality of Chinese Chemical Society & International Chiral Meeting
    • Place of Presentation
      中国、長家界
    • Year and Date
      2012-08-03
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体への固相状態でのキラリティー誘起2012

    • Author(s)
      下村昂平, 前田勝浩, 井改知幸, 加納重義, 八島栄次
    • Organizer
      第61回高分子学会年次大会
    • Place of Presentation
      横浜
    • Year and Date
      2012-05-29
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖に動的キラルユニットを導入したポリアセチレン誘導体へのらせん誘起と記憶2012

    • Author(s)
      下村昂平, 前田勝浩, 井改知幸, 加納重義, 八島栄次
    • Organizer
      シンポジウムモレキュラー・キラリティーアジア2012
    • Place of Presentation
      福岡
    • Year and Date
      2012-05-17
    • Related Report
      2013 Final Research Report
  • [Presentation] 側鎖に動的キラルユニットを導入したポリアセチレン誘導体へのらせん誘起と記憶

    • Author(s)
      下村昂平・前田勝浩・井改知幸・加納重義・八島栄次
    • Organizer
      シンポジウム モレキュラー・キラリティー アジア 2012
    • Place of Presentation
      九州大学医学部百年講堂
    • Related Report
      2012 Research-status Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体への固相状態でのキラリティー誘起

    • Author(s)
      下村昂平・前田勝浩・井改知幸・加納重義・八島栄次
    • Organizer
      第61回高分子学会年次大会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Helicity Control of Polyacetylene Derivative Bearing Biphenyl Pendants and Its Application to Chiral Stationary Phases for HPLC

    • Author(s)
      ○Tomoyuki Ikai, Kouhei Shimomura, Katsuhiro Maeda, Shigeyoshi Kanoh, Eiji Yashima
    • Organizer
      The 5th Symposium on Molecular Chirality of Chinese Chemical Society & International Chiral Meeting
    • Place of Presentation
      Zhangjiajie of Hunan Province, China
    • Related Report
      2012 Research-status Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体へのらせん誘起と記憶

    • Author(s)
      下村昂平・前田勝浩・井改知幸・加納重義・八島栄次
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋工業大学
    • Related Report
      2012 Research-status Report
  • [Presentation] 側鎖にビフェニル基を有するポリアセチレン誘導体へのらせん誘起とその光学分割への応用

    • Author(s)
      下村昂平・前田勝浩・井改知幸・加納重義・八島栄次
    • Organizer
      第61回高分子学会北陸支部研究発表会
    • Place of Presentation
      福井大学
    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://kohka.ch.t.kanazawa-u.ac.jp/lab5/lab5.html

    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] 不斉選択性の切り替えが可能なクロマトグラフィー用充填剤2012

    • Inventor(s)
      前田勝浩, 井改知幸, 下村昴平
    • Industrial Property Rights Holder
      前田勝浩, 井改知幸, 下村昴平
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2012-109971
    • Filing Date
      2012-05-11
    • Related Report
      2013 Final Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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