Abstract
The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The final ADIL was obtained by a simple metathesis reaction of the corresponding dibromide ionic liquid, in turn prepared by alkylation of 3-(3-bromopropyl)-1-propylimidazolium bromide. The ADIL structure and those of its precursors were confirmed through NMR and infrared spectroscopy, and the thermal properties of all compounds were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Density, solubility, and viscosity were measured for the prepared compounds.
Highlights
Ionic liquids (ILs) are organic salts, liquid at room temperature or below 100 ◦ C, composed by an organic cation and an organic or an inorganic anion [1]
We describe the synthesis of a new asymmetrical dicationic ionic liquid (ADIL) characterized by both a pyrrolidinium and an imidazolium cation
We report a synthetic procedure for the synthesis of 1-octyl-3-(3-(1-methylpyrrolidiniumyl) propyl)imidazolium bis(trifluoromethane)sulfonimide, C3 (C8 Im)(C1 Pyrr)/2 Tf2 N (3)
Summary
Ionic liquids (ILs) are organic salts, liquid at room temperature or below 100 ◦ C, composed by an organic cation (e.g., imidazolium, ammonium, or phosphonium) and an organic or an inorganic anion [1]. DILs may present further external alkyl chains on the cation part and are characterized by two counteranions, which can be of the same kind or different kinds Because of these features, dicationic ILs (DILs) have been shown to possess superior tunability potential when compared to monocationic ILs, and this advantage has been exploited for designing DILs for specific applications; for example, DILs exhibited much higher thermal degradation temperatures [18,19], wider liquid ranges, higher densities, higher glass transition temperatures and melting points, larger surface tensions, higher shear viscosities [20], and electrochemical windows in the range of 4.3 V to 4.7 V [21].
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