Post-polymerisation functionalisation of polyethers by olefin cross metathesis

• Main Author: Morrison, Stephen
• Published: University of Glasgow 2017
• Subjects: 547; QD Chemistry
• Online Access: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.724043

Industrial uses of polyethers have expanded to medical applications, ranging from artificial tissues (i.e. implants, sutures and prosthetics), to the encapsulation of drugs; however post-polymerisation functionalisation methods are limited. Olefin cross metathesis (CM) is a powerful carbon-carbon bond forming reaction, and therefore could potentially conjugate polymers possessing pendent olefin handles. This could be of significant importance as the alkenes do not readily interfere with common polymerisation techniques such as anionic ring opening polymerisation (ROP), polyesterifications, or polyamidations. This project describes the synthesis of novel biocompatible polyethers with diverse pendent olefins and their cross metathesis reaction with a range of partners. These various polymers are designed to probe the possibility of preventing the occurrence of self metathesis upon functionalisation using Hoveyda-Grubbs’ second-generation catalyst. One such polymer has been proven to be immune to the undesired self metathesis pathway allowing for retention of the low polymer dispersity (Ɖ = 1.15). We have shown that the cell signalling peptide RGD can be coupled efficiently to this polymer.