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

Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2014-10-01

Journal: ELECTROPHORESIS

Included Journals: Scopus、PubMed、SCIE

Volume: 35

Issue: 19,SI

Page Number: 2752-2758

ISSN: 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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