Amino-functionalized polyesters (APEs) are a remarkable class of polymeric materials with a wide range of applications, e.g. as antibacterial materials, gene delivery carriers, and biodegradable plastics. However, the current APE synthetic pathway poses significant challenges in terms of structural diversity and control over polymerization. In recent years, ring-opening alternating copolymerization (ROAC) of epoxides and cyclic anhydrides has been demonstrated to be a powerful and versatile method for polyester synthesis via varying the binary combination of monomers. In this study, we successfully applied ROAC in APEs syntheses via utilizing cyclic anhydride with glycidylamine as an amino-functionalized epoxide, respectively (Figure 1).
The ROAC of cyclic anhydride and glycidylamine was conducted with an alcohol initiator based on the conditions of our previous work. The obtained products were characterized by 1H and 13C nuclear magnetic resonance (NMR) and size elusion chromatography (SEC). The molecular weight of the poly(phthalic anhydride-alt-dibenzylglycidylamine) was easy to control up to ca. 21,000 by adjusting the initial monomer-to-initiator ratio, while retaining the narrow dispersity (Đ < 1.19). Moreover, the versatility of the present APEs syntheses was demonstrated by applying various alcohol initiators, cyclic anhydrides, and glycidylamines, which successfully produced APEs with functional terminal end-group or different properties.