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

• DOI: 10.1002/chir.20756
• Publication Date: 2009-07-14T16:00:47Z
• Authors: Miao Li Luo; Wei Guang Zhang; Sheng Zhang; Jun Fan; Wen Cui Su; Xia Yin
• Keywords: Chiral discrimination; β-cyclodextrin; QCM; Aminoethanethiol; 540; 530; 01 natural sciences; UV; 0104 chemical sciences

AbstractA novel chiral sensor based on the self‐assembled monolayer of (6A‐ω‐mercaptoethylureado‐6A‐deoxy)heptakis(2,3‐di‐o‐phenylcarbamoyl)‐6B, 6C, 6D, 6E, 6F, 6G‐ hexa‐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. Chirality, 2010. © 2009 Wiley‐Liss, Inc.