A novel “one-pot” approach for the preparation of β-cyclodextrin functionalized monoliths and their application to enantioseparations — ASN Events
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A novel “one-pot” approach for the preparation of β-cyclodextrin functionalized monoliths and their application to enantioseparations (#131)

Qiaoxuan Zhang 1 , Jialiang Guo 1 , Jacques Crommen 1 2 , Zhengjin Jiang 1
  1. Department of Pharmacy, Jinan University, Guangzhou, China
  2. Laboratory of Pharmaceutical Analytical Chemistry, Department of Pharmaceutical Sciences, University of Liege, Liege, Belgium

The development of novel types of chiral stationary phases in HPLC still attracts considerable interest. Great efforts have been dedicated to the development of chiral monolithic capillary columns.

In this research, a novel and simple “one-pot” copolymerization approach was developed for the preparation of β-cyclodextrin (β-CD) functionalized organic polymer monoliths. The proposed scheme based on “one-pot” process comprises two major reactions occurring in sequence in the same vial: (1) ring opening reaction between the epoxy groups of glycidyl methacrylate (GMA) and the primary amino groups of ethylenediamine-β-CD (EDA-β-CD); (2) copolymerization of GMA-EDA-β-CD and ethylene dimethacrylate (EDMA) with 2,2’-azobisisobutyronitrile (AIBN) as the polymerization initiator.    

Compared to the previously reported two-step strategy, the monoliths prepared by this one-pot method exhibited higher β-CD ligand density and better column efficiency in HPLC. Satisfactory column permeability and separation performance were also obtained on the optimized poly(GMA-EDA-β-CD-co-EDMA) monolithic columns. Additionally, higher enantioresolution for a series of chiral acidic compounds was observed on these monoliths. This study opens up possibilities for preparing other monolithic columns that involve ring opening reaction between epoxy and primary amino groups.