TY - JOUR
T1 - Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer
T2 - A quantum chemical study
AU - Nishikawa, Tomohiro
AU - Torimoto, Tsukasa
AU - Nakanishi, Takuya
AU - Osaka, Tetsuya
AU - Ohtani, Bunsho
PY - 2006/12/11
Y1 - 2006/12/11
N2 - Structural and energetic investigations based on semiempirical PM5 and ab initio HF and MP2 calculations suggested that the self-assembled monolayer of an atropisomeric compound, (R)- or (S)-1,1′-binaphthalene-2,2′-dithiol (BNSH), on a gold (1 1 1) surface selectively adsorbs one enantiomer of phenylalanine (Phe), resulting in chiral discrimination, through hydrophobic, cation(-NH3+)-π and NH(Phe)-π (BNSH) interactions in a nanometer-sized screw-hole-like pocket composed of three BNSH molecules in the monolayer.
AB - Structural and energetic investigations based on semiempirical PM5 and ab initio HF and MP2 calculations suggested that the self-assembled monolayer of an atropisomeric compound, (R)- or (S)-1,1′-binaphthalene-2,2′-dithiol (BNSH), on a gold (1 1 1) surface selectively adsorbs one enantiomer of phenylalanine (Phe), resulting in chiral discrimination, through hydrophobic, cation(-NH3+)-π and NH(Phe)-π (BNSH) interactions in a nanometer-sized screw-hole-like pocket composed of three BNSH molecules in the monolayer.
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U2 - 10.1016/j.cplett.2006.10.106
DO - 10.1016/j.cplett.2006.10.106
M3 - Article
AN - SCOPUS:36448984932
SN - 0009-2614
VL - 432
SP - 502
EP - 507
JO - Chemical Physics Letters
JF - Chemical Physics Letters
IS - 4-6
ER -