Preparation of a hydroxypropyl-β-cyclodextrin functionalized monolithic column by one-pot sequential reaction and its application for capillary electrochromatographic enantiomer separation

In this study, a hydroxypropyl-β-cyclodextrin (HP-β-CD) functionalized monolithic capillary column was prepared by one-pot sequential reaction for the first time. The preparation of the HP-β-CD functionalized monolithic column involves two sequential reactions in one pot: (1) the ring opening reaction between HP-β-CD and glycidyl methacrylate (GMA) catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU); (2) the copolymerization of GMA-HP-β-CD, ethylene dimethacrylate (EDMA) and 2-acrylamido-2-methyl propane sulfonic acid (AMPS). A series of monolithic columns were successfully prepared by varying the temperature of the ring opening reaction or several copolymerization parameters (the type and composition of porogenic solvents, ratio of GMA-HP-β-CD to EDMA and polymerization temperature). Then, the morphologies and structures of the resulting monolithic stationary phases were characterized by optical microscopy, scanning electron microscopy (SEM) and nitrogen adsorption analysis. Raman spectroscopy clearly indicated the successful bonding of HP-β-CD onto the monolith. When the prepared chiral stationary phase (CSP) was applied for the separation of a set of racemic compounds by capillary electrochromatography (CEC), including racemic anticholinergic drugs, β-adrenergic drugs, meptazinol and its intermediates, satisfactory separation selectivities were obtained. Additionally, the column also showed excellent separation abilities towards four flavanone glycosides epimers. Furthermore, the prepared monolithic columns exhibited satisfactory stability and reproducibilities of retention time, resolution and column efficiency. These results demonstrated the potential and usefulness of the developed one-pot sequential strategy in the preparation of other derivatized CD functionalized monolithic columns.