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Studies on Asymmetric Synthesis, Structure, and Function of Optically Active Poly(methacrylamide) Derivatives

Research Project

Project/Area Number 17550116
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionNagoya University

Principal Investigator

OKAMOTO Yoshio  Nagoya University, EcoTopia Science Institute, Professor, エコトピア科学研究所, 教授 (60029501)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2006: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2005: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsHelix-Sense-Selective Polymerization / Methacrylamide / Radical Polymerization / Anionic Polymerization / Optically Active Polymer / Asymmetric Polymerization / 立体特異性重合 / らせん / メタクリアミド / M-(トリフェニルメチル)メタクリルアミド / N-フェニルメタクリルアミド
Research Abstract

1. The radical polymerization of the methacrylamides having a bulky side group, such as N-[(4-butyl)triphenylmethyl]methacrylamide (BuTrMAM) and N-[(4-butylphenyl)dibenzosuberyl]methacrylamide (BuPDBSMAM), in the presence of (+)-menthol or (-)-menthol was carried out in order to attain the helix-sense-selective polymerization leading to the optically active polymers. The tacticity of the polymers was estimated to be nearly 100% isotactic from the ^1H NMR spectra of the polymers in D_2SO_<4->. The circular dichroism (CD) spectra of the polymers suggested that the polymers have a helical conformation with an excess right-or left-handed helicity. The radical copolymerization of BuTrMAM with an optically active comonomer, such as N-[(R)-(+)-1-(1-naphthyl)ethyl]methacrylamide ((+)-NEMAM), was also carried out. The optical activity of the copolymers significantly depended on the comonomer contents. When (+)-NEMAM content was low in the copolymer, the (+)-NEMAM units effectively induced the one-handed helicity consisting of BuTrMAM monomeric sequences.
2. BuTrMAM was polymerized with the chiral anionic initiator systems consisting of n-Bu_4ZnLi_2 and halogeno sugars, such as 2,3,4,6-tetra-0-acetyl-α-D-galactopyranosyl bromide. The ^1H NMR spectra in D_2SO_4 suggested that the polymers were highly isotactic, and the initiating chain end of polymers has a sugar residue. The obtained polymers exhibited an optical activity, and the halogeno sugars affected the specific rotations and Cotton effect in the CD spectra. These results indicate that the polymers prepared by the n-Bu_4ZnLi_2/halogeno sugars initiator systems have a helical conformation with an excess right- or left-handed helicity.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (12 results)

All 2007 2006 2005

All Journal Article (12 results)

  • [Journal Article] Asymmetric radical polymerization and copolymerization of N-(1-phenyldibenzosuberyl) methacrylamide and its derivative leading to optically active helical polymers2007

    • Author(s)
      A.K.M.F.Azam
    • Journal Title

      J. Polym. Sci. Part A : Polym. Chem. 45(7)

      Pages: 1304-1315

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric radical polymerization and copolymerization of N-(1-phenyldibenzosuberyl)methacrylamide and its derivative leading to optically active helical polymers2007

    • Author(s)
      A.K.M.F.Azam, M.Kamigaito, Y.Okamoto
    • Journal Title

      J.Polym.Sci., Part A : Polym.Chem. 45(7)

      Pages: 1304-131

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric radical polymerization and copolymerization of N-(l-phenyldibenzosuberyl)methacrylamide and its derivative leading to optically active helical polymers2007

    • Author(s)
      A.K.M.F.Azam
    • Journal Title

      J. Polym. Sci. Part A : Polym. Chem. 45(7)

      Pages: 1304-1315

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Helix-Sense-Selective Free Radical Polymerization of N-(Triphenylmethyl)methacrylamide Derivatives2006

    • Author(s)
      A.K.M.F.Azam
    • Journal Title

      Polym. J. 38(10)

      Pages: 1035-1042

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Helicity Induction in N-[(4-Butyl)triphenylmethyl]methacrylamide Sequence via Radical Copolymerization with Chiral Monomers2006

    • Author(s)
      A.K.M.F.Azam
    • Journal Title

      Polym. J. 38(11)

      Pages: 1173-1181

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Helix-Sense-Selective Radical Polymerization of N-(Triphenylmethyl)methacrylamides and Properties of the Polymers2006

    • Author(s)
      N.Hoshikawa
    • Journal Title

      Polym. J. 38(12)

      Pages: 1258-1266

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Helix-Sense-Selective Free Radical Polymerization of N-[(Triphenylmethy1)methacrylamide Derivatives2006

    • Author(s)
      A.K.M.F.Azam, M.Kamigaito, Y.Okamoto
    • Journal Title

      Polym.J. 38(10)

      Pages: 1035-1042

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Helicity Induction in N-[(4-Butyl)triphenylmethyl]methacrylamide Sequence via Radical Copolymerization with Chiral Monomers2006

    • Author(s)
      A.K.M.F.Azam, M.Kamigaito, M.Tsuji, Y.Okamoto
    • Journal Title

      Polym.J. 38(11)

      Pages: 1173-1181

    • NAID

      10019372344

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Helix-Sense-Selective Radical Polymerization of N-(TriphenylmethyDmethacrylamides and Properties of the Polymers2006

    • Author(s)
      N.Hoshikawa, C.Yamamoto, Y.Hotta, Y.Okamoto
    • Journal Title

      Polym.J. 38(12)

      Pages: 1258-1266

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Helix-Sence-Selective Radical Polymerization oh N-(Triphenylmethyl)methacrylamide and Properties of the Polymers2006

    • Author(s)
      Naohiro Hoshikawa
    • Journal Title

      Polymer Journal (印刷中)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis, Chiroptical Properties, and Chiral Recognition Ability of Optically Active Polymethacrylamides Having Various Tacticities2005

    • Author(s)
      Kohei Morioka
    • Journal Title

      Polymer Journal 37

      Pages: 299-308

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Asymmetric Radical Polymerization of N-Phenylmethacrylamides2005

    • Author(s)
      Yuki Amano
    • Journal Title

      Polymer Journal 37

      Pages: 629-632

    • Related Report
      2005 Annual Research Report

URL: 

Published: 2005-04-01   Modified: 2016-04-21  

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