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Chiral stationary phases consisting of p-conjugated polymers bearing glucose-linked biphenyl units: Reversible switching of recognition abilities based on coil-to-helix transition

Research Project

Project/Area Number 26410129
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Polymer chemistry
Research InstitutionKanazawa University

Principal Investigator

Ikai Tomoyuki  金沢大学, 物質化学系, 准教授 (90402495)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords共役高分子 / スイッチング / キラリティー / グルコース / 高次構造 / 光学分割 / コンホメーション / 軸不斉
Outline of Final Research Achievements

An optically active p-conjugated polymer (poly-1) consisting of alternating thieno[3,4-b]thiophene and glucose-linked biphenyl units was synthesized. We found that poly-1 undergoes a conformational transition between random-coil and helix in both solution and the solid state in response to the external solvent environment. Coated-type chiral stationary phases (CSPs) were prepared from both the random-coil and helical poly-1, and the influence of the polymer backbone structure on chiral recognition ability was evaluated. The two CSPs showed complementary resolution abilities. In addition, an immobilized-type CSP with universal solvent durability was also prepared using an alkyne-appended poly-1 analogue and an azide-functionalized silica gel. The resulting CSP displayed repeatable switching of the chiral recognition ability based on a coil-to-helix transition of the polymer backbone by alternate column treatment with common organic solvents, such as chloroform and acetonitrile.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (17 results)

All 2017 2016 2015

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 2 results,  Acknowledgement Compliant: 9 results) Presentation (8 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] The Dawn of Chiral Material Development Using Saccharide-Based Helical Polymers2017

    • Author(s)
      Ikai, T.
    • Journal Title

      Polym. J.

      Volume: 49 Issue: 4 Pages: 355-362

    • DOI

      10.1038/pj.2016.123

    • NAID

      40021149946

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cellulose derivatives bearing pyrene-based π-conjugated pendants with circularly polarized luminescence in molecularly dispersed state2017

    • Author(s)
      Ikai, T.; Kojima, Y.; Shinohara, K.-i.; Maeda, K.; Kanoh, S.
    • Journal Title

      Polymer

      Volume: 117 Pages: 220-224

    • DOI

      10.1016/j.polymer.2017.04.032

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A cellulose-based chiral fluorescent sensor for aromatic nitro compounds with central, axial and planar chirality2017

    • Author(s)
      Ikai, T.; Suzuki, D.; Shinohara, K.-i.; Maeda, K.; Kanoh, S.
    • Journal Title

      Polym. Chem.

      Volume: 8 Issue: 14 Pages: 2257-2265

    • DOI

      10.1039/c7py00285h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and chiroptical properties of a [small pi]-conjugated polymer containing glucose-linked biphenyl units in the main chain capable of folding into a helical conformation2016

    • Author(s)
      Ikai, T.; Shimizu, S.; Awata, S.; Kudo, T.; Yamada, T.; Maeda, K.; Kanoh, S.
    • Journal Title

      Polymer Chemistry

      Volume: 7 Issue: 48 Pages: 7522-7529

    • DOI

      10.1039/c6py01759b

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants2016

    • Author(s)
      Ikai, T.; Suzuki, D.; Kojima, Y.; Yun, C.; Maeda, K.; Kanoh, S.
    • Journal Title

      Polymer Chemistry

      Volume: 7 Issue: 29 Pages: 4793-4801

    • DOI

      10.1039/c6py00967k

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Impact of a minority enantiomer on the polymerization of alanine-based isocyanides with an oligothiophene pendant2016

    • Author(s)
      Ikai, T.; Wada, Y.; Takagi, Y.; Shinohara, K.-i.
    • Journal Title

      Polymer Chemistry

      Volume: 7 Issue: 46 Pages: 7057-7067

    • DOI

      10.1039/c6py01351a

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of Amylose- and β-Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants2016

    • Author(s)
      Ikai, T.; Yun, C.; Kojima, Y.; Suzuki, D.; Maeda, K.; Kanoh, S
    • Journal Title

      Molecules

      Volume: 21 Issue: 11 Pages: 1518-1529

    • DOI

      10.3390/molecules21111518

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of novel glucose-based polymers and their applications as chiral stationary phases for high performance liquid chromatography2016

    • Author(s)
      Tomoyuki Ikai and Takayuki Yamada
    • Journal Title

      Chinese Journal of Chromatography

      Volume: 34 Issue: 1 Pages: 4-9

    • DOI

      10.3724/sp.j.1123.2015.10037

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of polyisocyanides bearing oligothiophene pendants: higher-order structural control through pendant framework design2015

    • Author(s)
      Tomoyuki Ikai, Yugaku Takagi, Ken-ichi Shinohara, Katsuhiro Maeda, and Shigeyoshi Kanoh
    • Journal Title

      Polymer Journal

      Volume: 47 Issue: 9 Pages: 625-630

    • DOI

      10.1038/pj.2015.42

    • NAID

      40020583087

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] グルコース連結型ビフェニルユニットを主鎖に含有する新規π共役高分子の合成とキラル固定相への応用2016

    • Author(s)
      粟田聖矢・清水祥・工藤知哉・井改知幸・前田勝浩・加納重義
    • Organizer
      第65回高分子学会年次大会
    • Place of Presentation
      神戸国際会議場・展示場 〒650-0046 兵庫県神戸市中央区港島中町6丁目9-1
    • Year and Date
      2016-05-25
    • Related Report
      2015 Research-status Report
  • [Presentation] π-Conjugated Polymers Containing Glucose-Linked Biphenyl Units2016

    • Author(s)
      井改知幸・清水祥・粟田聖矢・工藤知哉・前田勝浩・加納重義
    • Organizer
      超分子による革新的マテリアル開発の拠点形成国際シンポジウム
    • Place of Presentation
      しいのき迎賓館 石川県金沢市広坂2-1-1
    • Year and Date
      2016-03-10
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 天然物を出発原料に用いたキラル材料開発2016

    • Author(s)
      井改知幸
    • Organizer
      平成28年度北陸地区高分子若手研究会
    • Place of Presentation
      福井県坂井市三国町テクノポート
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] グルコース連結型ビフェニルユニットを含有する共役らせんポリマーの合成と機能性キラル材料への応用2015

    • Author(s)
      井改知幸・清水祥・粟田聖矢・工藤知哉・前田勝浩・加納重義
    • Organizer
      第25回日本MRS年次大会
    • Place of Presentation
      横浜情報文化センター 横浜市中区日本大通11
    • Year and Date
      2015-12-08
    • Related Report
      2015 Research-status Report
  • [Presentation] グルコース連結型ビフェニルユニットを含有する新規π共役高分子の合成とその円偏光発光特性2015

    • Author(s)
      清水祥・工藤知哉・井改知幸・前田勝浩・加納重義
    • Organizer
      第64回高分子学会北陸支部研究発表会
    • Place of Presentation
      石川ハイテク交流センター 石川県能美市旭台2丁目1
    • Year and Date
      2015-11-14
    • Related Report
      2015 Research-status Report
  • [Presentation] 単糖連結型ビフェニルユニットを含有する新規π共役高分子の合成とそのらせんキラリティー制御2015

    • Author(s)
      井改知幸・清水祥・工藤知哉・前田勝浩・加納重義
    • Organizer
      シンポジウム モレキュラー・キラリティー 2015
    • Place of Presentation
      早稲田大学西早稲田キャンパス
    • Year and Date
      2015-06-12 – 2015-06-13
    • Related Report
      2014 Research-status Report
  • [Presentation] グルコース連結型ビフェニルユニットを含有する新規π共役高分子の合成とそのキロプティカル特性2015

    • Author(s)
      清水祥・工藤知哉・山田貴之・井改知幸・前田勝浩・加納重義
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      2015-05-27 – 2015-05-29
    • Related Report
      2014 Research-status Report
  • [Presentation] グルコース連結型ビフェニルユニットを含有する新規π共役高分子の合成とそのキロプティカル特性2015

    • Author(s)
      清水祥・工藤知哉・山田貴之・井改知幸・前田勝浩・加納重義
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター 〒003-0006 札幌市白石区東札幌6条1丁目1-1
    • Year and Date
      2015-05-27
    • Related Report
      2015 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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