Electrophilic Aromatic Aroylation Polycondensation of Acyl-acceptor and Acyl-donor Molecules Composed of Binaphthylylene or Biphenylylene Aromatic Ring Assembly Units

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  • OKAMOTO Akiko
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • SHIKIJI Wataru
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • MAEYAMA Katsuya
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • OIKE Hideaki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • IMAIZUMI Masahiro
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • YONEZAWA Noriyuki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology

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Other Title
  • ビナフチリレン単位およびビフェニリレン単位を有するアシル受容体およびアシル供与体による親電子芳香族置換アシル化重縮合
  • ビナフチリレン タンイ オヨビ ビフェニリレン タンイ オ ユウスル アシル ジュヨウタイ オヨビ アシル キョウヨタイ ニ ヨル シンデンシ ホウコウゾク チカン アシルカジュウ シュクゴウ

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Abstract

Polymerization of 2,2′-dimethoxybiphenyl and 2,2′-dimethoxybis(1-naphthyl) as acyl-acceptor monomers and 2,2′-dimethoxybis(1-naphthylylene)-6,6′-dicarboxylic acid/-dicarbonyl chloride and 2,2′-dimethoxybiphenyl dicarboxylic acid/-dicarbonyl chloride as acyl-donor monomer in the electrophilic aromatic aroylation polycondensation is discussed. 2,2′-Dimethoxybis(1-naphthyl) only gave medium molecular weight aromatic polyketones by phosphorous pentoxide-methanesulfonic acid (P2O5-MsOH)-mediated electrophilic aromatic aroylation polycondensation with 2,2′-dimethoxybiphenyl and its dicarboxylic acid, whereas 2,2′-dimethoxybiphenyl has proved to be far more effective acyl-acceptant ability to give various aromatic polyketones with arenedicarboxylic acids/-dicarbonyl chlorides with the aid of trifluoromethanesulfonic acid (TfOH) or P2O5-MsOH. In general, the reactivity of acyl-acceptor monomer determines the susceptibility of electrophilic aromatic aroylation polycondensation. Furthermore, we could show that TfOH with arenedicarbonyl chloride has tolerable activity with sufficient selectivity and balanced reactivity, which is a requisite to promote this type of polycondensation.<br>

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 66 (4), 147-153, 2009

    The Society of Polymer Science, Japan

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