title: "Click" immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application.
abstract: Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido-beta-CD derivatives to alkynyl modified silica via "click" chemistry and applied to the HPLC enantioseparation of various chiral compounds. The perphenylcarbamated CD CSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcohols, flavonoids, bendroflumethiazide, atropine and some beta-blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide. The "click" chemistry immobilized permethylated CD CSP (CCM-CSP) afforded poor chiral recognition for most analytes, but could resolve non-aromatic ionone derivatives which were not separated on CCP-CSP. These results suggest that resolution with cyclodextrin derived CSPs depend on a complex interplay of 'host'-'guest' inclusion, hydrogen bonding, pi-pi and hydrophobic interactions.
authors.affiliation: School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore.
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
authors.forename: David J
authors.initials: DJ
authors.lastname: Young
authors.forename: Timothy Thatt Yang
authors.initials: TT
authors.lastname: Tan
authors.forename: Siu-Choon
authors.initials: SC
authors.lastname: Ng
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D003505:Cyclodextrins / Q000737:chemistry*; D006860:Hydrogen Bonding
chemical_list: D003505:Cyclodextrins