TY - JOUR
T1 - Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality
AU - Nakanishi, Takuya
AU - Yamakawa, Naoko
AU - Asahi, Toru
AU - Shibata, Norio
AU - Ohtani, Bunsho
AU - Osaka, Tetsuya
PY - 2004/8/3
Y1 - 2004/8/3
N2 - 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-alf of that caused by pure enantiomeric SAM.
AB - 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-alf of that caused by pure enantiomeric SAM.
KW - Binaphthalenedithiol
KW - Enantioselective adsorption
KW - Gold(111) surface
KW - Quartz crystal microbalance
KW - Self-assembled monolayer
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U2 - 10.1002/chir.20039
DO - 10.1002/chir.20039
M3 - Article
C2 - 15239071
AN - SCOPUS:3242704008
SN - 0899-0042
VL - 16
SP - S36-S39
JO - Chirality
JF - Chirality
IS - SUPPL.
ER -