Radical Polymerization Reaction of Styrene-Based Monomers Catalyzed by Iron Complexes Bearing β-Aminoketonato Ligand

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  • SAKAYORI Takafumi
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University
  • SATO Takashi
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University
  • NAGAYA Makoto
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University
  • YAMAGUCHI Takamichi
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University
  • ISHIHARA Shinji
    Instrumental Analysis Center, Yokohama National University
  • KANEKO Takeo
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University
  • YAMAGUCHI Yoshitaka
    Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University

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Other Title
  • β-アミノケトナト配位子を有する鉄錯体を用いたスチレン系モノマーのラジカル重合反応
  • v-アミノケトナト ハイイシ オ ユウスル テツ サクタイ オ モチイタ スチレンケイ モノマー ノ ラジカル ジュウゴウ ハンノウ
  • Radical Polymerization Reaction of Styrene-Based Monomers Catalyzed by Iron Complexes Bearing β-Aminoketonato Ligand

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Abstract

β-Aminoketone (2-H) was prepared by the condensation reaction of acetylacetone with aniline derivatives. Divalent iron complexes formulated as [Fe(Ar-β-aminoketonato)2] (Ar = 2,6-diisopropylphenyl: 3a, 2,4,6-trimethylphenyl: 3b, 2,6-dimethylphenyl: 3c, 4-methylphenyl: 3d) were prepared by the reaction of FeCl2 with two equivalents of Li(β-aminoketonato), which was prepared by the deprotonation of 2-H with n-BuLi in situ. X-Ray diffraction revealed that these iron complexes have a four-coordinate tetrahedral geometry around the iron center. The distortion from a tetrahedral geometry in the iron complexes 3 was influenced by substituents on the nitrogen atoms, i.e., a sterically encumbered substituent on the nitrogen atom caused more distortion from the normal tetrahedral geometry. Radical polymerization of styrene catalyzed by the iron complex (3) coupled with (1-bromoethyl)benzene as an initiator was examined. The iron complex 3c was found to be an efficient catalyst for the controlled radical polymerization of styrene. In order to elucidate the catalytic activity of iron complexes 3, the cyclic voltammograms of complexes 3 were measured and X-ray diffraction on trivalent iron complexes was performed. The pincer-type iron complex (1), having the tridentate β-aminoketonato scaffold, acted as an effective catalyst for the controlled radical polymerization of 4-chlorostyrene. Furthermore, the radical polymerization of 4-acetoxystyrene was also investigated.

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 72 (5), 306-317, 2015

    The Society of Polymer Science, Japan

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