Thiol-Ene Click Chemistry as a Tool for a Novel Family of Polymeric Ionic Liquids

Functionalized pyrrolidinium compounds, 3-((2-hydroxyethylthio)methyl)-1,1,4-trimethylpyrrolidinium and 3-((2-carboxyethylthio)methyl)-1,1,4-trimethylpyrrolidinium chlorides, are prepared from N,N-diallyl-N,N-dimethylammonium chloride by radical thiol-ene addition and are utilized as building blocks in the synthesis of ionic liquid-like monomers. Polymeric ionic liquids with highest molecular weights are obtained in water from chloride monomers followed by ionic exchange with lithium bis(trifluoromethylsulfonyl)imide. Synthesized polymers demonstrate negligible water absorption (<0.1 wt%). Copolymerization with polyethyleneglycol di- and monomethacrylates leads to the conductive self-standing tough films with ionic conductivity up to 2.8 x 10-7/1.3 x 10-6 S cm-1 at 25 degrees C.