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Clickable Poly(ionic liquids): A Materials Platform for Transfection
Author(s) -
Freyer Jessica L.,
Brucks Spencer D.,
Gobieski Graham S.,
Russell Sebastian T.,
Yozwiak Carrie E.,
Sun Mengzhen,
Chen Zhixing,
Jiang Yivan,
Bandar Jeffrey S.,
Stockwell Brent R.,
Lambert Tristan H.,
Campos Luis M.
Publication year - 2016
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.201605214
Subject(s) - cationic polymerization , ionic liquid , polymer , macromolecule , click chemistry , modular design , polyelectrolyte , materials science , polymerization , ionic bonding , biocompatible material , combinatorial chemistry , chemistry , chemical engineering , polymer chemistry , ion , organic chemistry , computer science , catalysis , biomedical engineering , medicine , biochemistry , operating system , engineering
The potential applications of cationic poly(ionic liquids) range from medicine to energy storage, and the development of efficient synthetic strategies to target innovative cationic building blocks is an important goal. A post‐polymerization click reaction is reported that provides facile access to trisaminocyclopropenium (TAC) ion‐functionalized macromolecules of various architectures, which are the first class of polyelectrolytes that bear a formal charge on carbon. Quantitative conversions of polymers comprising pendant or main‐chain secondary amines were observed for an array of TAC derivatives in three hours using near equimolar quantities of cyclopropenium chlorides. The resulting TAC polymers are biocompatible and efficient transfection agents. This robust, efficient, and orthogonal click reaction of an ionic liquid, which we term ClickabIL, allows straightforward screening of polymeric TAC derivatives. This platform provides a modular route to synthesize and study various properties of novel TAC‐based polymers.