A facile and efficient one-step strategy for the preparation of β-cyclodextrin monoliths

Abstract

A novel, facile, and efficient one-step copolymerization strategy was developed for the preparation of β-cyclodextrin (β-CD) methacrylate monolithic columns using click chemistry. The novel mono-(1H-1,2,3-triazol-4-ylmethyl)-2-methylacryl-β-CD monomer was synthesized by a click reaction between propargyl methacrylate and mono-6-azido-β-CD, and then monolithic columns were prepared through a one-step in situ copolymerization of the mono-(1H-1,2,3-triazol-4-ylmethyl)-2-methylacryl-β-CD monomer and ethylene dimethacrylate. The physicochemical properties and column performance of the fabricated monolithic columns were characterized by elemental analysis, SEM, and micro-HPLC. Satisfactory column permeability, efficiency, and separation performance were obtained for the optimized poly(mono-(1H-1,2,3-triazol-4-ylmethyl)-2-methylacryl-β-CD-co-ethylene dimethacrylate) monolithic columns. Additionally, typical hydrophilic interaction chromatography retention behavior was observed on the monoliths at high acetonitrile content in the mobile phase. Although the enantioselectivity of our monolithic columns did not meet the level of other reported β-CD monolithic columns, this one-step strategy based on click chemistry still provides an interesting and effective model as it offers the possibility to easily prepare related novel CD methacrylate monoliths through a one-step copolymerization strategy.

Keywords: Click chemistry; Hydrophilic interaction liquid chromatography; Monolithic columns; β-Cyclodextrin.