A series of 1-vinyl-3-alkylimidazolium halide ([VRIM]X) and 1-vinyl-3-esterimidazolium chloride ([VEIM]-Cl) ionic liquids, a functional material with unsaturated bonds, were synthesized by using microwave-assisted synthesis method. The structures were characterized by 1 H NMR. Through Gaussian09/B3PW91/6-311G (2d,p) density functional methods, the interaction energies of ion pairs of [VRIM]X and [VEIM]Cl were obtained. The relationships between the surface tensions and temperature (293.15 to 333.15) K, molecular structure, and the interaction energies of ion pairs, etc. along with the relationships between the solubility and molecular structure, common solvents, and the interaction energies of ion pairs, etc. were discussed systematically. The results showed that surface tension decreased linearly with temperature and decreased with the elongation of the alkyl chain length on cation and the decrease of interaction energies of ion pairs. With decreasing dielectric constant of solvent or the increase of the anion size, the solubility of the title ionic liquids decreased. With the elongation of the alkyl chain length, the interaction energies of ion pairs decreased, and the solubility in polar solvents had decreasing trend. The relationship between the surface tensions and solubility parameter for [VRIM]Br was expressed by using Hildebrand−Scoff equation.
■ INTRODUCTIONIonic liquids (ILs) are organic salts at room temperature or less than 300°C which are entirely composed of an organic cation (imidazolium, pyridinium, tetraalkylammonium, etc.) and an anion such as halide, triflate, amidotriflate, dicyanamide, tetrafluoroborate, hexafluorophosphate, etc. 1 The ionic character implies the extraordinary high ion density, and thus leads to the negligible vapor pressure (i.e, wide liquid temperature range and negligible flammability) and high ionic conductivity. 2,3 A key feature of ILs is that their physicochemical properties can be tailored virtually at will by varying their cations, substituents, and anions. 4−6 Research on structure and properties of ILs are mainly focused on melting point, conductivity, density, thermal stability, etc. at present, 7−17 which provide some theoretical basis for the structure analysis of ILs, the design and synthesis of novel functionalized ILs. 18,19 In addition, ILs have better solubility and surface activity; thus, they have been widely used in many scientific fields. 20−27 However, studies on the surface tension and solubility of ILs are still scarce, and the surface tensions of only a few of ILs have been reported; 28−32 Previous studies mainly have been done on the qualitative analysis of the solubility of ILs in organic or inorganic solvents, with little attention paid to the quantitative analysis of their solubility and the general law of solubility; The surface tension and solubility for most common ILs mainly concentrates on several N-alkyl-N-methylimidazolium ILs. 33−37 None of these studies have investigated the surface tension and the quantitative analysis of the solubil...