A novel chiral sensor based on the self-assembled monolayer of (6(A)-omega-mercaptoethylureado-6(A)-deoxy)heptakis(2,3-di-0-phenylcarbamoyl)-6(B), 6(C), 6(D), 6(E), 6(F), 6(G)-hexa-0-phenylcarbamoyl-beta-cyclodextrin (Ph-beta-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 (6(A)-azido-6(A)-deoxy)heptakis(2,3-di-0-phenylcarbamoyl)-6(B), 6(C), 6(D), 6(E), 6(F), 6(G)-hexa-0-phenylcarbamoyl-beta-cyclodextrin (Ph-beta-CD) and (R,S)-(+/-)-(3-methoxyphenyl) ethylamine. The UV discrimination factor was determined to be 0.066. Chirality 22:411-415, 2010. (C) 2009 Wiley-Liss, Inc.