The development of degradable polymers is of significant interest across a wide range of fields from coatings to nanomedicine and tissue engineering. Much progress has been made to date with conventional polyesters such as polylactide and polycaprolactone. However, the ability to control the degradation of these polymers in different environments is limited and they may degrade more rapidly or more slowly than desired. Many stimuli-responsive polymers have been developed over the past couple of decades, but these polymers typically require many stimuli-mediated events to achieve complete backbone degradation. To address this limitation, our team has been developing self-immolative polymers, a new class of degradable polymers, that undergo end-to-end backbone depolymerization in response to the cleavage of a single end-cap from the polymer terminus, thereby affording amplification of the stimulus-mediated event. Self-immolative polyglyoxylate properties were tuned by varying the structures of the glyoxylate monomers to afford different pendant groups on the polymers or by performing post-polymerization functionalization. In addition, block copolymers were prepared using linker end-caps having additional functional groups and these were assembled into stimuli-responsive nanoscale vesicles and micelles. A diverse library of end-caps were developed that were responsive to stimuli including light, heat, pH changes, reducing agents, reactive oxygen species, and enzymes. Furthermore, amidation reactions were used to convert readily accessible poly(ethyl glyoxylate) to various polyglyoxylamides, which exhibit very different properties than the polyglyoxylates. The function of these degradable polymers was demonstrated through the incorporation and triggered release of drug molecules from surfactant-stabilized nanoparticles, micelles, and vesicles. In addition, polyglyoxylates were applied as coatings to release agricultural chemicals in response to stimuli. Overall, this work demonstrates the versatility and applicability of self-immolative polymers across a range of fields.

Self-immolative polymers: Designing structure, properties, and function

2019 Fall National Meeting

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