Self-assembly and chiral recognition of quartz crystal microbalance chiral sensor

Abstract

A novel chiral sensor based on the self-assembled monolayer of (6 A-ωmercaptoethylureado-6A-deoxy)heptakis(2,3-di-o- phenylcarbamoyl)-6B, 6C, 6D, 6E, 6F, 6Ghexa-o-phenylcarbamoyl-β-cyclodextrin (Ph-β-CD-SH) on a quartz crystal transducer for chiral recognition was set up. (R,S)-(±)-(3-Methoxyphenyl)ethylamine were recognized by this QCM chiral sensor with a QCM chiral discrimination factor of 1.33. Furthermore, UV spectroscopy was used to investigate the mechanism of host-guest interactions between (6A-azido-6A-deoxy)heptakis(2,3-di-o- phenylcarbamoyl)-6B, 6C, 6D, 6E, 6F, 6G-hexa-o-phenylcarbamoyl-β-cyclodextrin (Ph-β-CD) and (R,S)-(±)-(3-methoxyphenyl) ethylamine. The UV discrimination factor was determined to be 0.066. © 2009 Wiley-Liss, Inc.