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Precisely controlled copper(0)-catalyzed one-pot reaction: Concurrent living radical polymerization and click chemistry

Authors

  • Weidong Zhang,

    1. Center for Soft Condensed Matter Physics and Interdisciplinary Research, Soochow University, Suzhou 215006, China
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  • Gaojian Chen,

    1. Center for Soft Condensed Matter Physics and Interdisciplinary Research, Soochow University, Suzhou 215006, China
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  • Zhijun Hu,

    1. Center for Soft Condensed Matter Physics and Interdisciplinary Research, Soochow University, Suzhou 215006, China
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  • Wei Zhang,

    1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
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  • Zhengbiao Zhang,

    1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
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  • Xiulin Zhu

    Corresponding author
    1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
    • Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Department of Polymer Science and Engineering, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
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Abstract

Copper(0)-catalyzed one-pot reaction combining living radical polymerization and “click chemistry” was investigated. By precisely tuning reaction time, three novel well-defined polymers with different degree of carboxyl substitution, poly(propargyl methacrylate) (PPgMA), poly(1-(4-carboxyphenyl)-[1,2,3]triazol-4-methyl methacrylate) (PCTMMA), and poly(1-(4-carboxyphenyl)-[1,2,3]triazol-4-methyl methacrylate-co-propargyl methacrylate) (PCTMMA-co-PPgMA) were selectively obtained via Cu(0) powder/N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA) cocatalyzed LRP and click chemistry. In addition, gel permeation chromatography and 1H NMR analysis in conjunction with FTIR spectroscopy elucidate that one-pot process undergoes three steps due to a pronounced rate enhancement of click reaction: (1) generating new monomer, 1-(4-carboxyphenyl)-[1,2,3]triazol-4-methyl methacrylate (CTMMA); (2) copolymerization of two monomers (CTMMA and PgMA); (3) building homopolymer PCTMMA. Surprisingly, in contrast to typical Cu(I)-catalyzed atom transfer radical polymerization (ATRP), copper(0)-catalyzed one-pot reaction showed high carboxylic acid group tolerance. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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