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2013 Fiscal Year Final Research Report

Development of Asymmetric Polymer Catalysts Based on Controlled Helical Structure

Research Project

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Project/Area Number 23750123
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

IIDA Hiroki  名古屋大学, 工学(系)研究科(研究院), 講師 (30464150)

Project Period (FY) 2011 – 2013
Keywords機能性高分子 / キラリティ / 高分子不斉触媒 / 不斉識別 / らせん構造
Research Abstract

In this project, we have developed optically active helical polymers containing organocatalytic units as the pendant or main chain, and investigated their asymmetric organocatalysis and chiral recognition ability with the anticipation that the one-handed helical conformation would enhance the enantioselectivity and chiral recognition ability as compared to those of the corresponding random polymers and monomers. We have successfully synthesized a series of optically active helical polymers consisting of naturally-occurring riboflavin (vitamin B2) and cinchona alkaloid derivatives that function as asymmetric catalysts, chiral stationary phases for HPLC, and chiral sensory materials.

  • Research Products

    (18 results)

All 2014 2013 2012 2011 Other

All Journal Article (10 results) Presentation (4 results) Book (1 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Riboflavin-Based Fluorogenic Sensor for Chemo-and Enantioselective Detection of Amine Vapors2014

    • Author(s)
      Iida, H.; Miki, M.; Iwahana, S.; Yashima, E
    • Journal Title

      Chem. Eur. J

      Volume: 20 Pages: 4257-4262

  • [Journal Article] Photoswitchable Organocatalysis in Acylation of Alcohol Using Dithienylethene-Linked Azoles2013

    • Author(s)
      Iida, H.; Umebayashi, N.; Yashima, E
    • Journal Title

      Tetrahedron

      Volume: 69 Pages: 11064-11069

    • DOI

      10.1016/j.tet.2013.11.015

  • [Journal Article] Guest-Induced Unidirectional Dual Rotary and Twisting Motions of a Spiroborate-Based Double-Stranded Helicate Containing a Bisporphyrin Unit2013

    • Author(s)
      Yamamoto, S.; Iida, H.; Yashima, E
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 52 Pages: 6849-6853

    • DOI

      10.1002/anie.201302560

  • [Journal Article] Synthesis and Bifunctional Asymmetric Organocatalysis of Helical Poly (phenylacetylene)s Bearing Cinchona Alkaloid Pendants via a Sulfonamide Linkage2013

    • Author(s)
      Iida, H.; Tang, Z.; Yashima, E
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: 51 Pages: 2869-2879

    • DOI

      10.1002/pola.26678

  • [Journal Article] Main-Chain Optically Active Riboflavin Polymer for Asymmetric Catalysis and Its Vapochromic Behavior2012

    • Author(s)
      Iida, H.; Iwahana, S.; Mizoguchi, T.; Yashima, E
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 15103-15113

    • DOI

      10.1021/ja306159t

  • [Journal Article] Enantioseparation on Helical Poly (phenylacetylene)s Bearing Cinchona Alkaloid Pendants as Chiral Stationary Phases for HPLC2012

    • Author(s)
      Naito, Y.; Tang, Z.; Iida, H.; Miyabe, T.; Yashima, E
    • Journal Title

      Chem. Lett

      Volume: 41 Pages: 809-811

    • DOI

      10.1246/cl.2012.809

  • [Journal Article] Enantioseparation on Poly (phenyl isocyanide)s with Macromolecular Helicity Memory as Chiral Stationary Phases for HPLC2012

    • Author(s)
      Miyabe, T.; Iida, H.; Yashima, E
    • Journal Title

      Chem. Sci

      Volume: 3 Pages: 863-867

    • DOI

      10.1039/clsc00708d

  • [Journal Article] Remarkable Enhancement of the Enantioselectivity of an Organocatalyzed Asymmetric Henry Reaction Assisted by Helical Poly (phenylacetylene)s Bearing Cinchona Alkaloid Pendants via an Amide Linkage2012

    • Author(s)
      Tang, Z.; Iida, H.; Hu, H.-Y.; Yashima, E
    • Journal Title

      ACS Macro Lett

      Volume: 1 Pages: 261-265

    • DOI

      10.1021/mz200161s

  • [Journal Article] Synthesis of Helical Poly (phenylacetylene)s Bearing Cinchona Alkaloid Pendants and Their Application to Asymmetric Organocatalysis2011

    • Author(s)
      Miyake, G. M.; Iida, H.; Hu, H. -Y.; Tang, Z.; Chen, E. Y. X.; Yashima, E
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: 49 Pages: 5192-5198

    • DOI

      10.1002/pola.24988

  • [Journal Article] Oxidative Esterification, Thioesterification, and Amidation of Aldehydes by a Two-Component Organocatalyst System Using a Chiral N-Heterocyclic Carbene and Redox-Active Riboflavin2011

    • Author(s)
      Iwahana, S.; Iida, H.; Yashima
    • Journal Title

      E. Chem. Eur. J

      Volume: 17 Pages: 8009-8013

    • DOI

      10.1002/chem.201100737

  • [Presentation] 機能性部位を導入したらせん高分子の創製と触媒的不斉合成への応用2013

    • Author(s)
      飯田拡基
    • Organizer
      有機分子触媒による未来型分子変換-第2回有機分子触媒若手セミナー
    • Place of Presentation
      ラフォーレ倶楽部伊東温泉湯の庭,静岡県
    • Year and Date
      20130914-15
  • [Presentation] らせん構造を活かした機能性キラル材料の開発2013

    • Author(s)
      飯田拡基
    • Organizer
      平成24年度名古屋コンファレンス『有機電子機能化学の最前線』
    • Place of Presentation
      名古屋大学,愛知県
    • Year and Date
      2013-03-11
  • [Presentation] 機能性分子を導入した光学活性らせん高分子の合成と応用2013

    • Author(s)
      飯田拡基
    • 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
      金沢大学,石川県
    • Year and Date
      2013-03-08
  • [Presentation] Main-Chain Optically Active Riboflavin Polymer for Asymmetric Catalysis and Its Vapochromic Behavior2012

    • Author(s)
      H.Iida, S. Iwahana, T. Mizoguchi and E. Yashima
    • Organizer
      The 9th SPSJ International Polymer Conference (IPC2012)
    • Place of Presentation
      Kobe,Japan
    • Year and Date
      20121211-14
  • [Book] "Synthesis and Application of Helical Polymers with Macromolecular Helicity Memory", In "Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis", ed by S. Itsuno2011

    • Author(s)
      H. Iida, E. Yashima
    • Total Pages
      201-222
    • Publisher
      Wiley-VCH, Weinheim, Chapter 7
  • [Remarks]

    • URL

      http://helix.mol.nagoya-u.ac.jp

  • [Remarks] 受賞等 飯田拡基、高分子研究奨励賞(高分子学会)

  • [Patent(Industrial Property Rights)] 光学異性体用分離剤2013

    • Inventor(s)
      八島栄次、飯田拡基、タン チェンリン、内藤裕樹
    • Industrial Property Rights Holder
      ダイセル化学工業、名古屋大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特願2012-108689,PCT/JP2013/063134
    • Filing Date
      2013-05-10
    • Overseas

URL: 

Published: 2015-06-25  

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