Synthesis and Properties of Magnetic Aryl-Imidazolium Ionic Liquids with Dual Bronsted/Lewis Acidity

A series of unique tunable aryl-imidazolium magnetic ionic liquids (MILs) with dual acidity that contain both Bronsted and Lewis acidic sites (abbreviated as B-L MILs) were synthesized and characterized using nuclear magnetic resonance and mass spectrometry. Physical properties, such as thermal properties, magnetic susceptibility, and Bronsted and Lewis acidity, were measured. These properties were found to depend on the cation structure. These B-L MILs had good solubility in many organic solvents, good thermal stability, and low melting points, and exhibited magnet-like behavior. For these B-L MILs, the Bronsted acidity was measured using ultraviolet-visible (UV-Vis), and the Lewis acidity was measured using Fourier transform infrared spectroscopy (FTIR). The results showed that B-L MILs with an electron-withdrawing group in the aryl-imidazolium moiety had higher Bronsted acidity, whereas those with an electron-donating group had higher Lewis acidity. This type of ionic liquid, with both Bronsted and Lewis acidic sites, is expected to be a useful solvent and catalyst for organic reactions.