Thiol-Bromo Click Reaction for One-Pot Synthesis of Star-Shaped Polymers

Macromol Rapid Commun. 2021 Jan;42(2):e2000519. doi: 10.1002/marc.202000519. Epub 2020 Nov 18.

Abstract

Star-shaped polymers have unique physical properties and they are sought after materials in industry. However, the ease of synthesis is essential for translation of these materials into large-scale applications. Herein, a highly efficient synthetic method to prepare star-shaped polymers by combination of Cu-mediated reversible deactivation radical polymerization (Cu-RDRP) and thiol-bromo click reaction is described. Well-defined linear and block polymers with a very high bromine chain end fidelity are obtained via Cu-RDRP and subsequently react with multi-functional thiol compounds. High coupling efficiencies of larger than 90% are obtained owing to the quick and efficient reaction between thiols and alkyl bromides. Moreover, the arms of the obtained star-shaped polymers are linked via thioether bonds to the core, making them susceptible for oxidative degradation.

Keywords: Cu-mediated RDRP; Star polymers; click reactions; one pot reactions; thiol-bromo.

MeSH terms

  • Bromine
  • Polymerization
  • Polymers*
  • Sulfhydryl Compounds*
  • Sulfides

Substances

  • Polymers
  • Sulfhydryl Compounds
  • Sulfides
  • Bromine