Functionalizable, Side Chain-Immolative Poly(benzyl ether)s

Abstract

Herein, we report a poly(benzyl ether)-based self-immolative polymer (SIP) with pendant pyridine disulfide groups. Cleavage of the side-chain disulfides leads to the formation of phenolates, which initiate depolymerization from the side chain. Due to the higher density of the disulfide groups compared to that of the chain-end-capping group, which normally is responsible for initiating depolymerization of SIPs, the side chain-immolative polymer (ScIP) can be readily degraded in the solid state where the mobility of polymer chains is substantially limited. The ScIP was also further modified through the thiol-disulfide exchange reaction to prepare ScIP-<i>g</i>-poly(ethylene glycol) graft polymers and organogels, which were also able to undergo complete reductive self-immolative degradation.