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Selenium-substituted carbonates as mediators for controlled radical polymerization

Authors

  • Jindong Zeng,

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

    1. Department of Polymer Science and Engineering, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, People's Republic of China
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  • Jian Zhu,

    Corresponding author
    • Department of Polymer Science and Engineering, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, People's Republic of China
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  • Nianchen Zhou,

    1. Department of Polymer Science and Engineering, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, People's Republic of China
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  • Zhenping Cheng,

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

    Corresponding author
    • Department of Polymer Science and Engineering, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, People's Republic of China
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Correspondence to: J. Zhu (E-mail: chemzhujian@suda.edu.cn) or X. Zhu (E-mail: xlzhu@suda.edu.cn)

ABSTRACT

A series of selenium-substituted carbonates, S,Se-dibenzyl dithioselenocarbonate (DTSC), S,Se-dibenzyl thiodiselenocarbonate (TDSC), and Se,Se-dibenzyl triselenocarbonate (TSC), were synthesized and used as mediators in radical polymerization. The results indicate that these selenium-substituted carbonates can control the polymerization of styrene (St) and methyl acrylate, as evidenced by the number-average molecular weight that increased linearly with the monomer conversion, molecular weights that agreed well with the predicted values, and successful chain extensions. The treatment of the resultant polystyrene by hydrogen peroxide generated polymers with approximately half-reduced molecular weights, and the absence of carbonate groups and vinyl double bond-terminated chain ends. The polymerization with these selenium-substituted carbonates was the same polymerization mechanism as their analogue, the widely used S,S-dibenzyl trithiocarbonate. This work provided a flexible protocol to incorporate selenium into the polymer chain backbone. Specifically, the treatment of these polymers by oxidation produced “clickable” vinyl-terminated chain ends, which provided possibilities for further functionalization, for example, via a thiol-ene click reaction. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2606–2613

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