title: Preparation of a β-cyclodextrin functionalized monolith via a novel and simple one-pot approach and application to enantioseparations.
abstract: A novel and facile one-pot copolymerization approach was developed for the preparation of a β-cyclodextrin (β-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-β-CD (EDA-β-CD); (2) the copolymerization of glycidyl methacrylate-ethylenediamine-β-CD (GMA-EDA-β-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 β-CD ligand density and better column efficiency in HPLC. Satisfactory column permeability and separation selectivity were also obtained on the optimized poly(GMA-EDA-β-CD-co-EDMA) monolithic column. Additionally, the column was also applied to the enantioseparation of some racemic acidic compounds with promising results.
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Qiaoxuan
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Jialiang
authors.initials: J
authors.lastname: Guo
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Wang
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China; Laboratory of Analytical Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, University of Liege, CHU B36, Liege B-4000, Belgium.
authors.forename: Jacques
authors.initials: J
authors.lastname: Crommen
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China. Electronic address: jzjjackson@hotmail.com.
authors.forename: Zhengjin
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004852:Epoxy Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D007536:Isomerism; D008689:Methacrylates / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D005029:Ethylenediamines; D008689:Methacrylates; D047392:beta-Cyclodextrins; C557802:ethylene-diamine-beta-cyclodextrin; C004919:ethylene dimethacrylate; C007870:glycidyl methacrylate
keywords: Cyclodextrin; Enantioseparation; Monolithic column; One-pot strategy