Tripodal “click” ligands for copper-catalyzed ATRP

Authors

  • Preeyanuch Sangtrirutnugul,

    Corresponding author
    1. Faculty of Science, Department of Chemistry, Center for Catalysis, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
    • Faculty of Science, Department of Chemistry, Center for Catalysis, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
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  • Purmpoon Maisopa,

    1. Faculty of Science, Department of Chemistry, Center for Catalysis, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
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  • Laksamee Chaicharoenwimolkul,

    1. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry, NANOCAST Laboratory, Mahidol University, Bangkok 10400, Thailand
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  • Atchariya Sunsin,

    1. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry, NANOCAST Laboratory, Mahidol University, Bangkok 10400, Thailand
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  • Ekasith Somsook,

    1. Faculty of Science, Department of Chemistry, Center for Catalysis, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
    3. Faculty of Science, Department of Chemistry, NANOCAST Laboratory, Mahidol University, Bangkok 10400, Thailand
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  • Vichai Reutrakul

    1. Faculty of Science, Department of Chemistry, Center for Catalysis, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
    2. Faculty of Science, Department of Chemistry and Center of Innovation in Chemistry, Mahidol University, Bangkok 10400, Thailand
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Abstract

A series of tris(R-methyltriazolylmethyl)amines [R = C6H5 (1), 4-FC6H4 (2), 4-MeOC6H4 (3), Fc (4)] were prepared and used as ligands for catalytic ATRP of methyl methacrylate (MMA). Despite a lower activity, the CuBr/4 catalyst promoted relatively well controlled polymerization compared to CuBr/1, as evidenced by narrower polydispersity indices. Meanwhile, no polymerization activity was observed with CuBr/2 and CuBr/3 under the catalytic conditions investigated. The CV measurements of CuBr2 complexes supported 1 and 4 in DMSO showed E1/2 values of –0.206 and –0.224 V, respectively, confirming the more electron-rich nature of CuBr/4. Although both CuBr/1 and CuBr/4 catalysts were only partially soluble in several organic solvents used, kinetic studies revealed a pseudo first order linear plot of ln[M]0/[M]t versus time. Addition of CuBr2 into the polymerization systems led to a decrease in polymer polydispersities and the observed rate constants (kobs). © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

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