The fabrication of block copolymer (BCP) vesicles (polymersomes) exhibiting synchronized covalent crosslinking and bilayer permeabilization remains a considerable challenge as crosslinking typically leads to compromised membrane permeability. Herein it is demonstrated how to solve this dilemma by employing a stimuli-triggered crosslinking strategy with amphiphilic BCPs containing photolabile carbamate-caged rimary amines. Upon self-assembling into polymersomes, light-triggered self-immolative decaging reactions release primary amine moieties and xtensive amidation reactions then occur due to suppressed amine pKa within hydrophobic milieu. This leads to serendipitous vesicle cross-linking and the process is associated with bilayer hydrophobicity-to-hydrophilicity transition and membrane perme-abilization.

Concurrent block copolymer polymersome stabilization and bilayer permeabilization by stimuli-regulated “traceless” crosslinking

249th National Meeting (2015)

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