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

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

Y Wang, David James Young, T T Y Tan and S C Ng
Journal of Chromatography A, Vol.1217(31), pp.5103-5108
2010
DOI: https://doi.org/10.1016/j.chroma.2010.06.003
url
https://doi.org/10.1016/j.chroma.2010.06.003View
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Abstract

"Click" chemistry chiral stationary phases enantioseparation β-Cyclodextrin
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.

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Biochemical Research Methods
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