title: Thioether bridged cationic cyclodextrin stationary phases: Effect of spacer length, selector concentration and rim functionalities on the enantioseparation.
abstract: The preparation and evaluation of four single thioether bridged cationic cyclodextrin (CD) chiral stationary phases (CSPs) with different spacer length, selector concentration and rim functionalities are reported. Mono-6-(1-vinyl/allyl/butenylimidazolium)-β-CDs chloride were synthesized and clicked onto thiol silica to form three novel cationic native-CD-CSPs (CSP1, CSP2 and CSP3) and a post-synthetic phenylcarbamoylation of CSP2 was performed affording CSP4. The enantioseparation ability of the as-prepared CSPs were evaluated in high performance liquid chromatography (HPLC) by separating over forty enantiomers including isoxazolines, dansyl amino acids, flavonoids, tröger's base, 4-chromanol, bendroflumethiazide and styrene oxide. Most of the enantiomers were well resolved with the resolution (Rs) of 4NPh-OPr reaching 12.68. The effects of spacer length, selector concentration and rim functionalities on the enantioseparation were investigated. A comparison of the current CSP with a commercial column (Cyclobond I 2000) was also conducted to reveal the superiors enantioselectivity of the as-prepared CSPs.
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
authors.forename: Xiaoxuan
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
authors.forename: Xuan
authors.initials: X
authors.lastname: Jin
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
authors.forename: Xiaobin
authors.initials: X
authors.lastname: Yao
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China. Electronic address: maxiaofei@tju.edu.cn.
authors.forename: Xiaofei
authors.initials: X
authors.lastname: Ma
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China. Electronic address: wangyongtju@tju.edu.cn.
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
mesh_terms: D000596:Amino Acids / Q000302:isolation & purification; D002412:Cations; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D057930:Click Chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D005419:Flavonoids / Q000302:isolation & purification; D007555:Isoxazoles / Q000302:isolation & purification; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D049971:Thiazides / Q000302:isolation & purification
chemical_list: D000596:Amino Acids; D002412:Cations; D003505:Cyclodextrins; D005419:Flavonoids; D007555:Isoxazoles; D013438:Sulfhydryl Compounds; D013440:Sulfides; D049971:Thiazides; D012822:Silicon Dioxide
keywords: Cationic cyclodextrin; Chiral stationary phase; High performance liquid chromatography; Thiol-ene click chemistry