Synthesis of ionic liquids functionalized β-cyclodextrin-bonded chiral stationary phases and their applications in high-performance liquid chromatography

Four novel ILs functionalized β-cyclodextrins (β-CDs) were prepared by treating 6-tosyl-β-cyclodextrin with 1,2-dimethylimidazole or 1-amino-1,2,3-triazole, and bonded to silica gel to obtain chiral stationary phases (CSPs) to be used in high-performance liquid chromatography (HPLC). The separation performances of these CSPs were examined with 16 chiral aromatic alcohol derivatives and 2 racemic drugs in acetonitrile-based polar-organic mobile phase. Excellent enantioseparations were achieved for most of the analytes. The highest value of resolution factor calculated is 6.868. Comparison of the performance of 8a, 8b, 8c and 8d suggests that the positively charged imidazole group provides electrostatic interactions probably through strong H-bonding with the analytes, whereas the cationic triazole, which forms a weaker ion pair with its counter ion, is more capable of participating in ion-pairing interactions with acidic analytes. However, for compounds 12 and 13, which have larger molecular volumes than the other analytes, the interactions between analytes and both cationic imidazole and its counter ion of the selectors play an important role in the chiral resolution. Moreover, the high resolutions were found to depend on the properties of the cations and anions on the selectors in combination with the chiral recognition sites on the rim of the CD. The ionic strength in mobile phase affects the relative interactions between analytes and the chiral selector as well as between analytes and solvents.