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Helix-Sense-Selective Radical Polymerization of Methacrylamides

Research Project

Project/Area Number 14350485
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionNagoya University

Principal Investigator

OKAMOTO Yoshio  Nagoya Univ., Grad.School of Eng., Professor, 工学研究科, 教授 (60029501)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥12,400,000 (Direct Cost: ¥12,400,000)
Fiscal Year 2003: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 2002: ¥8,400,000 (Direct Cost: ¥8,400,000)
KeywordsHelical Polymer / Isotactic-Specific Polymerization / Methacrylamides / Radical Polymerization / Asymmetric Polymerization / Helix-Sense-Selective Polymerization
Research Abstract

In this study, the radical polymerization of N-(triphenylmethyl)methacrylamide (TrMAM) and N-[di(4-butylphenyl)phenylmethyl]-methacrylamide (DBuTrMAM) was carried out in order to attain the helix-sense-selective polymerization leading to optically active polymers. The radical polymerization of TrMAM and DBuTrMAM proceeded in an isotactic-specific manner, and the ^1H NMR spectra of the obtained polymers in D_2SO_4 indicated that the obtained polymers were almost 100% isotactic polymers, which may produce an equimolar mixture of left-and right-handed helices. The poly(DBuTrMAM)s prepared in chiral menthols were optically active, and the polymerization in (+)-menthol and (-)-menthol produced the polymers having the negative and positive specific rotation, respectively. In the circular dichroism (CD) spectra of the poly(DBuTrMAM)s synthesized in menthols at 0℃, the peak patterns suggested that the polymer having an excess single-handed helicity was produced. Although poly(TrMAM)s were insoluble in common organic solvents, the analogous CD patterns were observed in Nujol in for the poly(TrMAM)s obtained in menthols. Triphenylmethyl methacrylate is easily solvolyzed in 10 minutes in methanol-chloroform at 35℃, but TrMAM was quite stable for the solvolysis for a week. Thus, the optically active poly(TrMAM) must afford a much stable chiral stationary phase against alcoholic solvents.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (21 results)

All Other

All Publications (21 results)

  • [Publications] S.Habaue, Y.Isobe, Y.Okamoto: "Stereocontrolled Radical Polymerization of Acrylamides and Methacrylamides Using Lewis Acids"Tetrahedron. 58. 8205-8209 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Isobe, Y.Suito, S.Habaue, Y.Okamoto: "Stereocontrol during Free-Radical Polymerization of Methacrylamides in the Presence of Lewis Acids"Journal of Polymer Science Part A : Polymer Chemistry. 41. 1027-1033 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe: "Lewis Acid-Catalyzed Tacticity Control during Radical Polymerization of (Meth)acrylamides"ACS Symposium Series. 854. 59-71 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Morioka, Y.Suito, Y.Isobe, S.Habaue, Y.Okamoto: "Synthesis and Chiral Recognition Ability of Optically Active Poly{N-[(R)-a-methoxycarbonylbenzyl]methacrylamide} with Various Tacticity by Radical Polymerization Using Lewis Acids"Journal of Polymer Science Part A : Polymer Chemistry. 41. 3354-3360 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Hoshilawa, Y.Hotta, Y.Okamoto: "Stereospecific Radical Polymerization of N-Triphenylmethylmethacrylamides Leading to Highly Isotactic Heelical Polymers"Journal of American Chemical Society. 125. 12380-12381 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Suito, Y.Isobe, S.Habaue, Y.Okamoto: "Isotactic-Specific Radical Polymerization of Methacrylamides in the Presence of Lewis Acids"Journal of Polymer Science, Part A : Polymer Chemistry. 40. 2496-2500 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe, T.Nakano: "Stereocontrol in Radical Polymerization of Acrylic Monomers"Macromolecular Symposia. 183. 83-88 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Habaue, Y.Isobe, Y.Okamoto: "Stereocontrolled Radical Polymerization of Acrylamides and Methacrylamides Using Lewis Acids"Tetrahedron. 58. 8205-8209 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] B.Ray, Y.Isobe, K.Morioka, S.Habaue, Y.Okamoto, M.Kamigaito, M.Sawamoto: "Synthesis of Isotactic Poly(N-isopropylacrylamide) by RAFT Polymerization in the Presence of Lewis Acid"Macromolecules. 36. 543-545 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Isobe, Y.Suito, S.Habaue, Y.Okamoto: "Stereocontrol during Free-Radical Polymerization of Methacrylamides in the Presence of Lewis Acids"Journal of Polymer Science, Part A : Polymer Chemistry. 41. 1027-1033 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe, Y.Suito: "Stereocontrol Using Lewis Acids in Radical Polymerization"Macromolecular Symposia. 195. 75-80 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe: "Lewis Acid-Catalyzed Tacticity Control during Radical Polymerization of (Meth)acrylamides"ACS Symposium Series 854. 59-71 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Hoshikawa, Y.Hotta, Y.Okamoto: "Stereospecific Radical Polymerization of N-Triphenylmethylmethacrylamides Leading to Highly Isotactic Helical Polymers"Journal of American Chemical Society. 125. 12380-12381 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Morioka, Y.Suito, Y.Isobe, S.Habaue, Y.Okamoto: "Synthesis and Chiral Recognition Ability of Optically Active Poly{N-[(R)-α-methoxycarbonylbenzyl]-methacrylamide} with Various Tacticities by Radical Polymerization Using Lewis Acids"Journal of Polymer Science, Part A : Polymer Chemistry. 41. 3354-3360 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] B.Ray, Y.Isobe, K.Matsumoto, S.Habaue, Y.Okamoto, M.Kamigaito, M.Sawamoto: "RAFT Polymerization of N-Isopropylacrylamide in the Absence and Presence of Y(OTf)_3 : Simultaneous Control of Molecular Weight and Tacticity"Macromolecules. 37. 1702-1710 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Isobe, Y.Suito, S.Habaue, Y.Okamoto: "Stereocontrol during Free-Radical Polymerization of Methacrylamides in the Presence of Lewis Acids"Journal of Polymer Science Part A : Polymer Chemistry. 41. 1027-1033 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe, Y.Suito: "Stereocontrol Using Lewis Acids in Radical Polymerization"Macromolecular Symposia. 195. 75-80 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Okamoto, S.Habaue, Y.Isobe: "Lewis Acid-Catalyzed Tacticity Control during Radical Polymerization of (Meth)acrylamides"ACS Symposium Series. 854. 59-71 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Morioka, Y.Suito, Y.Isobe, S.Habaue, Y.Okamoto: "Synthesis and Chiral Recognition Ability of Optically Active Poly{N-[(R)-a-methoxycarbonylbenzyl]methacrylamide} with Various Tacticity by Radical Polymerization Using Lewis Acids"Journal of Polymer Science Part A : Polymer Chemistry. 41. 3354-3360 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] N.Hoshilawa, Y.Hotta, Y.Okamoto: "Stereospecific Radical Polymerization of N-Triphenylmethylmethacrylamides Leading to Highly Isotactic Heelical Polymers"Journal of American Chemical Society. 12380. 12380-12381 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] B.Ray, Y.Isobe, K.Matsumoto, S.Habaue, Y.Okamoto, M.Kamigaito, M.Sawamoto: "RAFT Polymerization of N-Isopropylacrylamide in the Absence and Presence of Y(OTf)_3 : Simultaneous Control of Molecular Weight and Tacticity"Macromolecules. 37. 1702-1710 (2004)

    • Related Report
      2003 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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