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Oxidative polymerization of 2,6-dimethylphenol to form poly(2,6-dimethyl-1,4-phenylene oxide) in water through one water-soluble copper(II) complex of a zwitterionic calix[4]arene

Authors

  • Li-Min Wan,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Hong-Xi Li,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Wei Zhao,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Hong-Ye Ding,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Yang-Yang Fang,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Pei-Hong Ni,

    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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  • Jian-Ping Lang

    Corresponding author
    1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 210032, People's Republic of China
    • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
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Abstract

In the presence of excess NaOH, reaction of Cu(OAc)2·H2O with equimolar ammonium calix[4]arene [H4L]I4 (1, H4L = [5,11,17,23-tetrakis(trimethylammonium)-25,26,27,28-tetrahydroxycalix[4]arene]) resulted in the formation of a mononuclear cationic Cu(II) complex [Cu(II)L(H2O)]I2 (2) in 43% yield. Complex 2 was characterized by elemental analysis, infrared (IR), and single crystal X-ray diffraction. The Cu(II) atom in 2 is coordinated by four oxygen atoms of one L4− ligand and one O atom from one water molecule, forming a square pyramidal geometry. Complex 2 exhibited high catalytic activity in the oxidative polymerization of 2,6-dimethylphenol using O2 as oxidizing agent in water under mild conditions. The selective polymerization produced poly(2,6-dimethyl-1,4-phenylene oxide) in high yields with almost no diphenoquinone. The influence of the polymerization temperature, the time interval, the molar ratio of 2,6-dimethylphenol/2, the concentrations of sodium hydroxide, and sodium n-dodecyl sulfate were examined. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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