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Synthesis of dendrimers through divergent iterative thio-bromo “Click” chemistry

Authors

  • Brad M. Rosen,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
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  • Gerard Lligadas,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
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  • Christian Hahn,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
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  • Virgil Percec

    Corresponding author
    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
    • Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Pennsylvania 19104-6323, Philadelphia
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Abstract

The development of a novel nucleophilic thio-bromo “Click” reaction, specifically base-mediated thioetherification of thioglycerol with α-bromoesters, is reported. Combination of this thio-bromo click reaction with subsequent acylation with 2-bromopropionyl bromide provides an iterative two-step divergent growth approach to the synthesis of a new class of poly(thioglycerol-2-propionate) (PTP) dendrimers. This approach is demonstrated in the rapid preparation of four generation (G1–G4) of PTP dendrimers with high-structural fidelity. The isolated G1–G4 bromide-terminated dendrimers can be used directly as dendritic macroinitiators for the synthesis of star-polymers via SET-LRP. Additionally, the intermediate hydroxy-terminated dendrimers are analogs of other water-soluble polyester and polyether dendrimers. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3931–3939, 2009

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