Preparation of a β-cyclodextrin functionalized monolith via a novel and simple one-pot approach and application to enantioseparations

A novel and facile one-pot copolymerization approach was developed for the preparation of a beta-cyclodextrin (beta-CD) functionalized organic polymer monolith. The proposed one-pot process involved two major reactions occurring in sequence in the same vial: (1) the ring opening reaction between the epoxy groups of glycidyl methacrylate (GMA) and the primary amino groups of ethylenediamine-beta-CD (EDA-beta-CD); (2) the copolymerization of glycidyl methacrylate-ethylenediamine-beta-CD (GMA-EDA-beta-CD) and ethylene dimethacrylate (EDMA) using 2,2'-azobisisobutyronitrile (AIBN) as the polymerization initiator. This approach avoids the time-consuming post-polymerization derivatization of the traditional two-step strategy. Compared to the previously reported two-step strategy, the monolith prepared by this one-pot method exhibited higher beta-CD ligand density and better column efficiency in HPLC. Satisfactory column permeability and separation selectivity were also obtained on the optimized poly(GMA-EDA-beta-CD-co-EDMA) monolithic column. Additionally, the column was also applied to the enantioseparation of some racemic acidic compounds with promising results. (C) 2013 Elsevier B.V. All rights reserved.