Thiol-ene click chemistry as a tool for a novel family of polymeric ionic liquids

摘要

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 × 10 ~(-7)/1.3 × 10 ~(-6) S cm ~(-1) at 25 °C. Radical thiol-ene addition was applied for the synthesis of functional pyrrolidinium ionic liquids and ionic monomers thereof. The advantages of approach are the use of water as green solvent, satisfactory yields, simplicity of reaction, and isomeric purity of products. New polymeric ionic liquids with ester fragments were then obtained and studied.