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

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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
Volume432
Issue number4-6
DOIs
Publication statusPublished - 2006 Dec 11

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phenylalanine
Self assembled monolayers
Phenylalanine
discrimination
Enantiomers
enantiomers
screws
thiols
Gold
Cations
Monolayers
gold
cations
Molecules
molecules
interactions
dithiol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Surfaces and Interfaces
  • Condensed Matter Physics

Cite this

Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer : A quantum chemical study. / Nishikawa, Tomohiro; Torimoto, Tsukasa; Nakanishi, Takuya; Osaka, Tetsuya; Ohtani, Bunsho.

In: Chemical Physics Letters, Vol. 432, No. 4-6, 11.12.2006, p. 502-507.

Research output: Contribution to journalArticle

Nishikawa, Tomohiro ; Torimoto, Tsukasa ; Nakanishi, Takuya ; Osaka, Tetsuya ; Ohtani, Bunsho. / Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer : A quantum chemical study. In: Chemical Physics Letters. 2006 ; Vol. 432, No. 4-6. pp. 502-507.
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