Synthesis of Polymer-Supported Homosalen Ligand and its Application to Stereoselective Polymerization of Racemic Lactide

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  • NOMURA Nobuyoshi
    Laboratory of Polymer Chemistry, Graduate School of Bioagricultural Sciences, E1–1(300), Nagoya University
  • HASEGAWA Jun
    Laboratory of Polymer Chemistry, Graduate School of Bioagricultural Sciences, E1–1(300), Nagoya University
  • KISHIDA Hisanori
    Business & Product Development Center, Environment, Energy & Plant Headquarters, Hitachi Zosen

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Other Title
  • 固定化ホモサレン配位子の合成とラセミラクチドの立体選択的重合反応への応用
  • コテイカ ホモサレン ハイイシ ノ ゴウセイ ト ラセミラクチド ノ リッタイ センタクテキ ジュウゴウ ハンノウ エ ノ オウヨウ

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Three polymer-supported homosalen ligands for the stereoselective polymerization of racemic lactide were synthesized: the Ph-substituted and tBu-substituted ligand on the Merrifield resin and the tBu-substituted ligand on the Wang resin. The corresponding aluminum catalyst was prepared by mixing with Et3Al in toluene at 70°C. Excess Et3Al was efficiently removed together with the solvent from the catalyst mixture. All of the catalysts stereoselectively polymerized racemic lactide to afford isotactic poly(racemic lactide)s, which were partially crystalline. Among the three examined catalysts, the tBu-substituted homosalen-Al catalyst on the Merrifield resin gave the most crystalline poly(racemic lactide), which showed a melting peak in the DSC measurement in the second run. Because of the immobilization of the catalyst on the resin, the obtained poly(racemic lactide) was colorless and never included the ligand-derived organic compounds in the polymer. The ligand resin was collected by filtration and was reusable.

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 70 (12), 744-752, 2013

    The Society of Polymer Science, Japan

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