In the present research, 1-ethyl-3-methyl-4-vinylimidazolium trifluoromethane sulfonate (triflate) was synthesized and polymerized. For comparative purposes, 1-ethyl-3-vinylimidazolium triflate and its polymer was also prepared. Zwitterionic propane sulfonate derivatives of 1-methyl-5-vinylimidazole and 1-vinylimidazole were also synthesized and polymerized. Poly(1-ethyl-3-methyl-4-vinylimidazolium triflate) and poly(3-ethyl-1-vinylimidazolium triflate) were characterized by means of TGA, GPC, and DSC. The TGA showed that poly(1-ethyl-3-methyl-4-vinylimidazolium triflate) had a higher decomposition temperature range, 467-527oC, than poly(3-ethyl-1-vinylimidazolium triflate), 400-448oC. Poly(styrene) equivalent molecular weights were evaluated by GPC in DMF. Poly(1-ethyl-3-methyl-4-vinylimidazolium triflate) had a Mn = 13,000 g/mol (Mw = 14,500 g/mol, PD = 1.11) and poly(3-ethyl-1-vinylimidazolium triflate) had a Mn = 15,700 g/mol (Mw = 19,000 g/mol, PD = 1.21). Glass transition characteristics were evaluated by DSC. Poly(3-ethyl-1-vinylimidazolium triflate) exhibited an onset Tg of 127-129oC; that for poly(1-ethyl-3-methyl-4-vinylimidazolium triflate) was 115oC. The 1-vinylimidazolium triflate polymer was anion exchanged to create a family of polymers with anions consisting of (CN)2N-, (CF3SO2)2N-, BF4-, PF6-, AsF6-, CF3SO3-. This family of polymer salts was characterized by DSC and the lowest onset Tg 84oC, was exhibited by the (CF3SO2)2N- salt. In the salts with fluorinated anions of similar geometry, the larger the anion, AsF6-, exhibited an onset Tg of 119oC. The polymer with the smaller PF6- anion exhibited an onset Tg, of 172oC. A copolymer of 1-ethyl-3-methyl-4-vinylimidazolium triflate and 1-methyl-5-vinylimidazole was synthesized. This copolymer was also anion-exchanged to create a family of polymers with (CN)2N-, (CF3SO2)2N-, BF4-, PF6-, AsF6-, CF3SO3 anions. DSC analysis of this family of copolymers revealed a similar trend in onset glass transition temperatures to that observed with the poly(1-ethyl-3-vinylimidazolium) salts.
Library of Congress Subject Headings
Ionic solutions; Polymerization
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Smith, Darren, "Synthesis and characterization of poly(ionic liquids) derived from 1-ethyl-3-methyl-4- vinylimidazolium triflate" (2011). Thesis. Rochester Institute of Technology. Accessed from
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