The Synthesis and Application of Polyglyoxylamides
Abstract
Self-immolative polymers (SIPs) are a subset of degradable polymers that can be triggered to fully depolymerize with a single stimulus event. This amplifying behaviour makes them ideal for real-world applications including sensors, recyclable plastics, and drug delivery vehicles. Polyglyoxylates (PGs) are a class of SIPs that can be synthesized in a one-pot reaction and designed to respond to different stimuli including light, heat, reduction, and oxidation. However, with the exception of poly(ethyl glyoxylate) (PEtG), the various glyoxylate monomers must be prepared and purified before polymerization, which can be difficult. Furthermore, PGs typically possess properties such as water-insolubility and low glass transition temperatures that make them unsuited for certain applications. This thesis details the synthesis of a new class of SIPs known as polyglyoxylamides (PGAms). PGAms were prepared from precursor PEtGs using post-polymerization amidation reactions with high conversion. The resulting polymers possessed properties differing from the precursor PEtGs, while still remaining capable of self-immolation. Furthermore, the synthetic method to create PGAms allowed for their properties to be easily tuned. This feature was taken advantage of in subsequent work, where PGAms were developed with a variety of properties including thermo- and pH-responsiveness. Furthermore, PGAms were developed that could form nanovesicles that may potentially serve as drug delivery vehicles and non-viral polycationic agents to assist with the transfection of nucleic acids.