Journal
CHIRALITY
Volume 16, Issue -, Pages S36-S39Publisher
WILEY
DOI: 10.1002/chir.20039
Keywords
enantioselective adsorption; self-assembled monolayer; binaphthalenedithiol; quartz crystal microbalance; gold(111) surface
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Chiral discrimination between thalidomide enantiomers was achieved using the self-assembled monolayer (SAM) of an atropisomeric compound, 1,1'-binaphthalene-2,2'-dithiol (BNSH), which takes a two-dimensional chiral arrangement on gold (111) surface. Interestingly, an all-or-none type enantioselectivity appears; one enantiomeric form of BNSH SAM allows the adsorption of only one enantiomer of thalidomide. In addition, the response of a racemic SAM of BNSH was revealed to be one-half of that caused by pure enantiomeric SAM. (C) 2004 Wiley-Liss, Inc.
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