Synthesis and Degradation of Photo-triggered Self-Immolative Poly(disulfides)
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The demand for responsive and degradable polymers is ever increasing to address the global environmental challenges faced by the abundant use of plastics and thermosets. Here, we examine poly(disulfide) (PDS) with various architectures containing poly(benzylcarbamate) (PBC) self-immolative units that can undergo triggered and controlled degradation. Using ortho-nitrobenzyl ester (o-NBE) as a photoreactive trigger, UV irradiation resulted in self-immolation of PBC chains to produce 4-aminophenol as a monomeric product with weak basicity that further facilitates cascade degradation of PDS chains. As disulfides are relatively strong covalent bond yet show dynamic nature in response to various stimuli, additional degradation process was examined by introducing heat and reductive thiols to effectively control the degradation kinetics and show reprocessibility.