Preparation of three regioisomeric ionic liquid stationary phases and investigation of their retention behavior

Abstract

The structural properties of ionic liquid stationary phases have a considerable effect on their separation selectivity. However, the difference of the chromatographic retention behavior of different regioisomeric ionic liquid stationary phases has rarely been investigated. In this study, three regioisomeric ionic liquid silane reagents were prepared by photoinitiated ene-click chemistry and bonded to silica by one-pot method to fabricate three new stationary phases (Sil-C2Im-C8, Sil-C6Im-C4, and Sil-C9Im-C1). All three stationary phases showed promising retention repeatability and efficiency. The retention behavior of the three stationary phases was investigated under various chromatographic conditions. The retention mechanism was further investigated by the linear energy solvation relationship and Van't Hoff plots. The stationary phases exhibited mixed-mode retention mechanisms. The π–π, hydrogen bonding, ion-exchange, and hydrophilic interactions with analytes were the weakest when the imidazole ions were embedded in the innermost part of the alkyl chains, while the interactions were the strongest when the imidazole ions were embedded in the middle of the alkyl chains. The three stationary phases provided great but different separation performances towards nucleosides, nucleobases, aromatic acids, alkyl benzenes, and polycyclic aromatic hydrocarbons due to the influence of imidazole ion position.