Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

Recently, we reported a new chiral stationary phase prepared using beta-cyclodextrin functionalized with aromatic ionic liquid which is aimed to enhance the performance of enantioseparation of flavonoids and beta-blockers. In this paper, the characteristics and performance of previously prepared chiral stationary phase denoted as beta-CD-BIMOTs were compared with the newly synthesized chiral stationary phase denoted as beta-CD-DIMOTs beta-CD-DIMOTs were prepared by functionalization of beta-cyclodextrin with aliphatic ionic liquid. The obtained beta-CD-BIMOTs and beta-CD-DIMOTs stationary phases were compared with native beta-CD stationary phase for the enantioseparation of non-steroidal anti-inflammatory drugs (NSAIDs) (ibuprofen, indoprofen, ketoprofen and fenoprofen). The beta-CD-BIMOTs stationary phase showed greater chiral resolution capabilities rather than beta-CD-DIMOTs and native beta-CD stationary phases. Further, in order to understand the interaction of enantioseparation, the inclusion complex formation between NSAIDs and beta-CD-BIMOTs was studied using H-1 NMR, NOESY and UV/Vis. The enantioseparated NSAIDs were found to form multiple interactions with beta-CD-BIMOTs-CSP.