Fluorinated Polymer Zwitterions: Choline Phosphates and Phosphorylcholines

Among zwitterionic structures, the choline phosphate (CP) group is uniquely attractive for its ability to access novel chemical compositions that embed functional groups directly into the zwitterionic moiety. This paper describes the attachment of fluorinated alkyl groups to CP moieties, yielding zwitterionic monomers 1 and 2 that proved amenable to controlled free radical polymerization and the production of a new set of CP-containing fluorinated polymers and copolymers with phosphorylcholine (PC) zwitterions. This combination of fluorinated hydrocarbons and zwitterions affords novel, water-soluble polymeric amphiphiles that we have examined at fluid interfaces, as coatings, in cell culture, and in magnetic resonance imaging.