Functional films from unsaturated poly(macrolactones) by thiol–ene cross-linking and functionalisation

Abstract

Macrolactones are naturally occurring materials, which can be polymerized into polymers with interesting properties. Here the possibility of synthesizing functional films derived from the unsaturated macrolactone globalide was systematically investigated employing thiol–ene chemistry. The most feasible method involved enzymatic polymerization of the monomer, followed by thiol–ene type cross-linking and surface functionalisation of the film. Evidence of the successful reactions was obtained from FTIR and FT Raman spectroscopy following the chemical modification of the polymer double bonds. Moreover, surface amine functionalisation was achieved by thiol–ene grafting 2-(Boc-amino)ethanethiol onto the poly(globalide) surface and subsequent deprotection. The possibility of further conjugation was demonstrated by reaction of the surface amino groups with fluorescein isothiocyanate (FITC). The as-obtained films provide an example of a renewable and degradable material platform with the potential of property enhancement for advanced applications.