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A novel fluorine-containing graft copolymer bearing perfluorocyclobutyl aryl ether-based backbone and poly(methyl methacrylate) side chains

Authors

  • Hao Liu,

    1. Key Laboratory of Organofluorine Chemistry and Laboratory of Polymer Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China
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  • Yongjun Li,

    1. Key Laboratory of Organofluorine Chemistry and Laboratory of Polymer Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China
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  • Sen Zhang,

    1. Key Laboratory of Organofluorine Chemistry and Laboratory of Polymer Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China
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  • Dong Yang,

    Corresponding author
    1. Key Laboratory of Molecular Engineering of Polymers (Ministry of Education), Laboratory of Advanced Materials and Department of Macromolecular Science, Fudan University, 220 Handan Road, Shanghai 200433, People's Republic of China
    • Key Laboratory of Molecular Engineering of Polymers (Ministry of Education), Laboratory of Advanced Materials and Department of Macromolecular Science, Fudan University, 220 Handan Road, Shanghai 200433, People's Republic of China
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  • Jianhua Hu,

    1. Key Laboratory of Molecular Engineering of Polymers (Ministry of Education), Laboratory of Advanced Materials and Department of Macromolecular Science, Fudan University, 220 Handan Road, Shanghai 200433, People's Republic of China
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  • Xiaoyu Huang

    Corresponding author
    1. Key Laboratory of Organofluorine Chemistry and Laboratory of Polymer Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China
    • Key Laboratory of Organofluorine Chemistry and Laboratory of Polymer Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China
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Abstract

A series of novel graft copolymers consisting of perfluorocyclobutyl aryl ether-based backbone and poly(methyl methacrylate) side chains were synthesized by the combination of thermal [2π + 2π] step-growth cycloaddition polymerization of aryl bistrifluorovinyl ether monomer and atom transfer radical polymerization (ATRP) of methyl methacrylate. A new aryl bistrifluorovinyl ether monomer, 2-methyl-1,4-bistrifluorovinyloxybenzene, was first synthesized in two steps from commercially available reagents, and this monomer was homopolymerized in diphenyl ether to provide the corresponding perfluorocyclobutyl aryl ether-based homopolymer with methoxyl end groups. The fluoropolymer was then converted to ATRP macroinitiator by the monobromination of the pendant methyls with N-bromosuccinimide and benzoyl peroxide. The grafting-from strategy was finally used to obtain the novel poly(2-methyl-1,4-bistrifluorovinyloxybenzene)-g-poly(methyl methacrylate) graft copolymers with relatively narrow molecular weight distributions (Mw/Mn ≤ 1.46) via ATRP of methyl methacrylate at 50 °C in anisole initiated by the Br-containing macroinitiator using CuBr/dHbpy as catalytic system. These fluorine-containing graft copolymers can dissolve in most organic solvents. This is the first example of the graft copolymer possessing perfluorocyclobutyl aryl ether-based backbone. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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