Enzymatic synthesis, post-polymerization modification and cross-linking of functionalized poly(β-thioether ester) with pendant vinyl group

Vinyl-functionalized poly(beta-thioether ester) (PVTE) was synthesized by enzyme-catalyzed polymerization using immobilized lipase B from Candida antarctica (CALB) for the first time. Four different functionalized monomers were prepared and three polymerization strategies including polycondensation (PC), ring-opening polymerization (ROP), and ring-opening and condensation copolymerization (ROCCP) were investigated. The influences of reaction conditions such as polymerization temperature, time, and monomer ratio on the molecular weight of functionalized poly(beta-thioether ester)s were also studied. Both the homopolymer and copolymers were characterized by NMR, SEC, TGA and DSC. Moreover, these poly(beta-thioether ester)s containing pendant double bonds toward postfunctionalization were demonstrated by photoinitiated thiol-ene click chemistry and Michael addition reaction, providing a way to cross-linked polyester gels.

Automated summary

Vinyl-functionalized poly(beta-thioether ester) (PVTE) was successfully synthesized using immobilized lipase B from Candida antarctica (CALB) by enzyme-catalyzed polymerization. Four different functionalized monomers and three polymerization strategies were investigated. The influences of reaction conditions on the molecular weight of functionalized poly(beta-thioether ester)s were studied. The homopolymer and copolymers were characterized and demonstrated the possibility of postfunctionalization.