title: Synthesis of novel perphenylcarbamated β-cyclodextrin based chiral stationary phases via thiol-ene click chemistry.
abstract: Novel cyclodextrin (CD) chiral stationary phases (CD-CSPs) with well-defined structure have been successfully synthesized by immobilization of mono/di(10-undecenoyl)-perphenylaminocarbonyl β-CD on the 3-mercaptopropyl functionalized silica gel via thiol-ene click chemistry. The phenyl carbamate groups on the rims of CD extended the cavity of CD-CSPs, which facilitated the formation of inclusion complex with various types of racemic compounds under RP mode, and also improved the π-π stacking interaction, dipole-dipole interaction, and hydrogen bonding interaction with racemic compounds under normal phase mode. Fifteen racemic compounds were successfully separated on this CD-CSP with HPLC, and the chromatographic results also demonstrated that thiol-ene click chemistry affords a facile approach for preparation of CSPs.
authors.affiliation: CAS Key Laboratory of Separation Science for Analytical Chemistry, National Chromatographic R&A Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Dalian, P. R. China; University of Chinese Academy of Sciences, Beijing, P. R. China; State Key Laboratory of Fine Chemicals and Department of Analytical Chemistry, Dalian University of Technology, Dalian, P. R. China.
authors.forename: Guang
authors.initials: G
authors.lastname: Huang
authors.forename: Junjie
authors.initials: J
authors.lastname: Ou
authors.forename: Xiaodan
authors.initials: X
authors.lastname: Zhang
authors.forename: Yongsheng
authors.initials: Y
authors.lastname: Ji
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Peng
authors.forename: Hanfa
authors.initials: H
authors.lastname: Zou
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D057930:Click Chemistry / Q000379:methods*; D015203:Reproducibility of Results; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D047392:beta-Cyclodextrins
keywords: Chiral stationary phases; Enantioseparation; HPLC; β-Cyclodextrin