Halogenation of Propagating Terminal in Anionic Polymerization of Isoprene for the Synthesis of Block Copolymers

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  • SATOH Kotaro
    Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University
  • MORI Yuya
    Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University
  • KAMIGAITO Masami
    Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University

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  • イソプレンのアニオン重合末端ハロゲン化を鍵としたブロック共重合体の合成
  • イソプレン ノ アニオン ジュウゴウ マッタン ハロゲンカ オ カギ ト シタ ブロック キョウ ジュウゴウタイ ノ ゴウセイ

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Abstract

<p>In this work, we investigated the direct halogenation of growing species in living anionic polymerization of hydrocarbon monomers for subsequent mechanistic transformation and post-polymerization reactions. The direct halogenation of propagating living anionic species of isoprene (Ip) was examined with CCl4 in THF/methylcyclohexane at −78°C to form a carbon-halogen terminal. The mechanistic transformation from living anionic into radical polymerization was then investigated using the anionically-prepared poly(Ip) (PIp) bearing a chloride terminal as the macroinitiator for the living radical polymerization with the RuCp*Cl(PPh3)/Et3N initiating system in toluene at 80°C, which resulted in the formation of block copolymers of PIp with various radically-polymerized segments. Furthermore, the terminal halogen of the anionically-prepared PIp was also converted into an azide group by SN2 reaction, which could be employed for the click reaction with alkyne-terminated poly(ethylene oxide) by a Cu catalyst to form an amphiphilic block copolymer.</p>

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 76 (3), 234-240, 2019-05-25

    The Society of Polymer Science, Japan

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