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Facile and Efficient One-Pot Transformation of RAFT Polymer End Groups via a Mild Aminolysis/Michael Addition Sequence

Authors

  • Xing-Ping Qiu,

    1. Department of Chemistry and Faculty of Pharmacy, University of Montreal, CP 6128 Succursale Centre Ville, Montreal, QC Canada H3C 3J7, Canada
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  • Françoise M. Winnik

    Corresponding author
    1. Department of Chemistry and Faculty of Pharmacy, University of Montreal, CP 6128 Succursale Centre Ville, Montreal, QC Canada H3C 3J7, Canada
    • Department of Chemistry and Faculty of Pharmacy, University of Montreal, CP 6128 Succursale Centre Ville, Montreal, QC Canada H3C 3J7, Canada. Fax: 1 514 340 3245
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Abstract

Summary: The trithiocarbonate end groups of polymers prepared by RAFT polymerization are converted into colorless and stable thioethers in a one-pot process that combines aminolysis of the trithiocarbonate functions and Michael addition of the resulting thiols to α, β-unsaturated carbonyl derivatives. This post polymerization procedure, which is carried out under mild conditions to near quantitative conversion, is described in the case of a telechelic poly(N-isopropylacrylamide) sample bearing isobutylsulfanylthiocarbonylsulfanyl end groups. The chemical composition, purity, and molar masses of the modified polymers are assessed by GPC, 1H NMR spectroscopy and UV-vis spectroscopy, which together demonstrate the efficiency of the method and confirm that the molecular weight and polydispersity of the precursor RAFT polymer are not affected by the treatment.

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The facile, one pot synthesis combines the reactions of trithiocarbonate aminolysis and Michael addition of a thiol to an α, β-unsaturated ester to transform the labile, colored thiocarbonylthio moiety into a stable, colorless thioether.

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