Synthesis and functionalization of thiol-reactive biodegradable polymers

Sebla Onbulak, Sarah Tempelaar, Ryan J. Pounder, Ozgul Gok, Rana Sanyal, Andrew P. Dove, Amitav Sanyal

Research output: Contribution to journalArticleResearchpeer-review

84 Citations (Scopus)

Abstract

A novel strategy to synthesize and functionalize maleimide containing thiol reactive biodegradable polymers by the organocatalyzed (co)polymerization of a novel furan-protected maleimide-functional carbonate monomer was described. The furan-protected maleimide-containing cyclic carbonate monomer was synthesized using the protected diol. Monitoring the monomer conversion with time in the DBU catalyzed homopolymerization revealed that the polymerization became retarded at ca. 60% monomer conversion, likely a consequence of the ring-chain equilibrium associated with sterically hindered monomers. The retro Diels-Alder reaction partially occurs upon ionization by the laser. Following exposure of the furan-protected copolymers to high vacuum at 100°C, the efficiency of the rDA reaction was clearly evident from the 1H NMR spectra of the polymers observing a complete disappearance of the resonances.

Original languageEnglish
Pages (from-to)1715-1722
Number of pages8
JournalMacromolecules
Volume45
Issue number3
DOIs
Publication statusPublished - 14 Feb 2012
Externally publishedYes

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