Functional aliphatic polyesters and nanoparticles prepared by organocatalysis and orthogonal grafting chemistry

Angela L. Silvers, Chia Chih Chang, Todd Emrick*

*Corresponding author for this work

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

We describe the use of organic catalysis for the ring-opening polymerization of functionalized lactones and conversion of the resulting aliphatic polyesters into crosslinked nanoparticles that carry additional functional groups amenable to further modification. Specifically, highly functional aliphatic polyester homopolymers, as well as random and block copolymers, were prepared by 1,5,7-triazabicyclo[4.4.0]dec-5-ene catalysis, giving polyesters with pendent alkene and alkyne groups. Azide-alkyne click and thiol-ene chemistries were used for postpolymerization modification of diblock copolymers possessing alkene groups on one block and alkyne groups on the other block. The polyesters were crosslinked using azide/alkyne cycloaddition, by reaction of α,ω-diazides with the pendent alkynes on the polyester backbone. This gave polyester nanoparticles possessing alkene functionality, which were subjected to further modification using thiol-ene reactions to introduce additional functionality.

Original languageEnglish
Pages (from-to)3517-3529
Number of pages13
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume50
Issue number17
DOIs
StatePublished - 1 Sep 2012

Keywords

  • 1,5,7-triazabicyclo[4.4.0]dec-5-ene
  • click chemistry
  • CuAAC
  • diblock copolymers
  • functional polyesters
  • nanoparticles
  • organocatalyst
  • polyesters
  • ring-opening polymerization
  • thiol-ene

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