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Synthesis of novel perphenylcarbamated beta-cyclodextrin based chiral stationary phases via thiol-ene click chemistry

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Indexed by:期刊论文

Date of Publication:2014-10-01

Journal:ELECTROPHORESIS

Included Journals:SCIE、PubMed、Scopus

Volume:35

Issue:19,SI

Page Number:2752-2758

ISSN No.:0173-0835

Key Words:Chiral stationary phases; beta-Cyclodextrin; Enantioseparation; HPLC

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 -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 - 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.

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