Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Tomohiro Nishikawa, Tsukasa Torimoto, Takuya Nakanishi, Tetsuya Osaka, Bunsho Ohtani

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2 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)502-507
Number of pages6
JournalChemical Physics Letters
Issue number4-6
Publication statusPublished - 2006 Dec 11


ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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