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Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12382-6. doi: 10.1002/anie.201605214. Epub 2016 Aug 31.

Clickable Poly(ionic liquids): A Materials Platform for Transfection.

Author information

1
Department of Chemistry, Columbia University, 3000 Broadway, New York, NY, 10027, USA.
2
Department of Chemistry, Columbia University, 3000 Broadway, New York, NY, 10027, USA. tl2240@columbia.edu.
3
Department of Chemistry, Columbia University, 3000 Broadway, New York, NY, 10027, USA. lcampos@columbia.edu.

Abstract

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.

KEYWORDS:

click chemistry; gene delivery; ionic liquids; polyelectrolytes; polymers

PMID:
27578602
PMCID:
PMC6552664
DOI:
10.1002/anie.201605214
[Indexed for MEDLINE]
Free PMC Article

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