Polyglyoxylamides: Tuning Structure and Properties of Self-Immolative Polymers

• Published in: Macromolecules 2019-01, Vol.52 (1), p.262-270
• Main Authors: Sirianni, Quinton E. A, Rabiee Kenaree, Amir, Gillies, Elizabeth R
• Format: Article
• Language: English
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/acs.macromol.8b02616

Self-immolative polymers (SIPs) are a class of stimuli-responsive materials that undergo controlled end-to-end depolymerization in response to stimuli. Their unique degradation and amplification properties have made them of interest for a diverse array of applications including sensors, vehicles for controlled release, and transient objects. Thus far, a limited number of SIP backbones exist, each with its own advantages and limitations. We report here the preparation and study of polyglyoxylamides (PGAms) as a new class of SIPs. PGAms were synthesized by simple postpolymerization modifications of poly­(ethyl glyoxylate) (PEtG). While retaining the important stimuli-responsive depolymerization properties of polyglyoxylates, PGAms exhibited much different thermal properties, and some were even water-soluble. Furthermore, a depolymerizable PGAm analogue of poly­(ethylene glycol) was prepared, demonstrating the capability to synthesize more complex PGAm graft copolymers. Overall, PGAms are a new class of SIPs with unique combinations of physical, thermal, and degradative properties that provide avenues for novel applications.