Proton transport properties in an ionic liquid having a hydroxyl group

An ionic liquid having a hydroxyl group, choline bis(trifluoromethylsulfonyl)amide ([N(111(2OH))][N(Tf)(2)]), was synthesized to investigate the effect of hydroxyl groups on the proton transport. 1,1,1-Trifluoro-N-(trifluoromethylsulfonyl)methanesulfoneamide (HN(Tf)(2)) as a proton source was mixed with the choline derivative at various molar ratios. Their thermal properties, viscosities, and ionic conductivities were investigated. [N(111(2OH))][N(Tf)(2)] showed a melting point at 27 °C, and its thermal stability was higher than 400 °C. The viscosity of [N(111(2OH))][N(Tf)(2)]/HN(Tf)(2) mixtures increased as the acid molar fraction increased. The ionic conductivity of [N(111(2OH))][N(Tf)(2)] was 2.1 × 10(-3) S cm(-1) at 25 °C; the ionic conductivity monotonously decreased as the acid molar fraction increased. There was a clear correlation between the ionic conductivity and the viscosity for the mixtures of the choline derivative and the acid. PFG-NMR measurements were carried out to investigate the diffusion behavior of protons. Although the acid and the hydroxyl group were indistinguishable by (1)H NMR, the self-diffusion coefficient of the (1)H of the hydroxyl group and the acid was larger than those of other (1)H nuclei. This difference suggests that a fast intermolecular proton transfer exists between the hydroxyl group and the acid.