"Click" immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application

Yong Wang, David J. Young, Timothy Thatt Yang Tan, Siu Choon Ng

Research output: Contribution to journalArticle

Abstract

Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido-β-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 β-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, π-π and hydrophobic interactions.

Original languageEnglish
Pages (from-to)5103-5108
Number of pages6
JournalJournal of Chromatography A
Volume1217
Issue number31
DOIs
Publication statusPublished - 30 Jul 2010
Externally publishedYes

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