Efficient polymerization and post-modification of N- substituted eight-membered cyclic carbonates containing allyl groups

Alexander Y. Yuen, Amaury Bossion, Antonio Veloso, David Mecerreyes, James L. Hedrick, Andrew P. Dove, Haritz Sardon

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Aliphatic polycarbonates are promising materials in the biomedical field due to their low toxicity, biocompatibility, and biodegradability. A popular approach in obtaining these materials is through the organocatalyzed ring-opening polymerization (ROP) of cyclic carbonates. Functional polycarbonates can be obtained by (co)polymerizing allyl-functional cyclic monomers, which can be chemically modified via radical thiol-ene click reactions after the ROP process. To date, allyl-bearing 6-membered cyclic carbonates have been reported, however their polymerization kinetics are slow. In previous works, larger cyclic carbonates (e.g. N-substituted eight membered cyclic carbonates) have demonstrated superior reactivities over their smaller counterparts and hence, in this work, we investigated the preparation and ROP of two allyl bearing N-substituted eight membered cyclic carbonates. One of these monomers, with a pendent carbamate group, displayed substantially enhanced polymerization kinetics that allowed for efficient homopolymerizations and co-polymerizations with commercially available monomers (e.g. trimethylene carbonate, or TMC). Lastly, the polymers underwent almost quantitative post-polymerization modification via thiol-ene chemistry to yield different functionalized polycarbonates. We also demonstrated that the post-polymerization reaction could be used to form polycarbonate-based gels with multifunctional thiols.

Original languageEnglish
Pages (from-to)2458-2467
Number of pages10
JournalPolymer Chemistry
Volume9
Issue number18
Early online date27 Mar 2018
DOIs
Publication statusPublished - 14 May 2018

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Polymers and Plastics
  • Organic Chemistry

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