Synthesis and post-functionalization of a degradable aliphatic polyester containing allyl pendent groups

•Vinyl-functionalized polyesters were prepared by the copolymerization of commercially available monomers.•The mole fraction of ally pendent groups in the copolymer reached as much as 16.7%.•The resulting copolymer was successfully post-functionalized by thiol-end click, epoxidation, and bromination reactions.

Aliphatic polyesters have been widely used in environmental and biomedical engineering, but a lack of functional groups limits their applications. Here, we reported a facile approach to synthesize vinyl functional polyester via the ring opening copolymerization of ε-caprolactone (CL) and allyl glycidyl ether (AGE). NMR analysis confirmed the copolymeric structures and suggested that the copolymerization depended on the epoxide ring of AGE rather than vinyl group. The amount of AGE incorporated into the copolymers (FAGE) increased with the amount of epoxide monomer feed with a maximum incorporation of 16.7%. Increasing temperature helped AGE to incorporate into the copolymer, however, accompanying with lots amount of AGE homopolymers. The resulting copolymer was successfully post-functionalized by thiol-end click, epoxidation, and bromination reactions depending on the reactivity of pendent ally groups. This facile and efficient approach can be used to functionalize biodegradable polymers and synthesize some new polymers under mild conditions.

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