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Concurrent Block Copolymer Polymersome Stabilization and Bilayer Permeabilization by Stimuli‐Regulated “Traceless” Crosslinking
Author(s) -
Wang Xiaorui,
Liu Guhuan,
Hu Jinming,
Zhang Guoying,
Liu Shiyong
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310589
Subject(s) - polymersome , amphiphile , copolymer , bilayer , vesicle , chemistry , membrane , biophysics , lipid bilayer , amine gas treating , covalent bond , combinatorial chemistry , polymer chemistry , organic chemistry , biochemistry , polymer , biology
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 primary amines. Upon self‐assembling into polymersomes, light‐triggered self‐immolative decaging reactions release primary amine moieties and extensive amidation reactions then occur due to suppressed amine p K a within hydrophobic milieu. This leads to serendipitous vesicle crosslinking and the process is associated with bilayer hydrophobicity‐to‐hydrophilicity transition and membrane permeabilization.