Syntheses of Wholly Aromatic Polyketones Bearing Trifluoromethyl Side Groups via Electrophilic Aromatic Aroylation Polymerization: Design, Synthesis, and Polymerization of Some Monomers Adaptable to Subsequent Electrophilic Aromatic Aroylation Chain-elongation Reactions with Satisfactory Regioselectivity

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  • OKAMOTO Akiko
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology
  • HORIGUCHI Tadahiro
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology
  • MITSUI Ryosuke
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology
  • YONEZAWA Noriyuki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology

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Other Title
  • トリフルオロメチル基含有全芳香族ポリケトンの精密合成反応：位置選択的親電子芳香族置換アロイル化を分子鎖伸長反応とする高分子合成に適合するモノマーの設計，合成，および重合
  • トリフルオロメチルキ ガンユウ ゼンホウコウゾク ポリケトン ノ セイミツ ゴウセイ ハンノウ イチ センタクテキ シンデンシ ホウコウゾク チカン アロイルカ オ ブンシサ シンチョウ ハンノウ ト スル コウブンシ ゴウセイ ニ テキゴウスル モノマー ノ セッケイ ゴウセイ オヨビ ジュウゴウ

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Abstract

Syntheses of wholly aromatic polyketones bearing trifluoromethyl side groups by electrophilic aromatic aroylation polymerization have been performed with the aid of molecular design of acyl-acceptant and acyl-donor monomers, retro synthetic analyses and practical optimization of monomer syntheses, and optimization of polycondensation system based on the choice of acidic mediator. The wholly aromatic polyketones having biphenylylenedicarbonyl moieties substituted with one or two trifluoromethyl groups in the main chain were synthesized by stepwise constructions of the corresponding dicarboxylic acid equivalent monomers by electrophilic aromatic substitutions and/or aromatic couplings followed by phosphorus (V) oxide-methanesulfonic acid-mediated regioselective electrophilic aromatic aroylation polymerizations. The sequence of the wholly aromatic polyketone bearing an unsymmetrical biphenylylenedicarbonyl moiety was constructed by suitable arrangement of CF3 and methoxy groups on the monomers realizing satisfactory regioselectivity. The acyl-acceptant monomers bearing CF3 groups were designed and synthesized by introduction of CF3-bearing aryl moiety on the 2,2′-dioxybiphenylylene unit, which successfully gave wholly aromatic polyketones by trifluoromethanesulfonic acid-mediated electrophilic aromatic aroylation polymerization.<br>

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 64 (12), 849-862, 2007

    The Society of Polymer Science, Japan

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