Formation of chiral surface with enantiomeric tartaric acid on gemini-structured self-assembled monolayers

Shinobu Yokokawa, Kaoru Tamada, Masahiko Hara

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Chiral surfaces were prepared by L, D, and Meso-tartaric acids (TAs) adsorbed on geministructured self-assembled monolayers (SAMs) composed of ethylenebis [(12-mercaptododecyl) dimethyl ammonium bromide] (HS-gQA-SH). The formation and structure of the chiral surfaces were characterized by surface plasmon resonance spectroscopy (SPR) and Fourier transform infraredreflection adsorption spectroscopy (FTIR-RAS). The thickness of enantiomeric TA layers on the HS-gQA-SH SAM was estimated to be c.a. 5-6 Å regardless of their chirality, in good agreement with the height of TA molecules anchoring on the surface with two COOH groups. All the TAs on the HS-gQA-SH SAM exhibit the same ionization state independent of their chirality in their vibration bands of carboxyiic groups. We attempted a second-layer adsorption of the enantiomeric TAs on L-TA monomolecular layer (L-TA SAM) precomposed on the HS-gQA-SH. A strong affinity between first and second TA layers resulted in the film growth when their chirality is identical (i.e., L-TA on L-TA SAM). We found the structure of second L-TA layer was completely different from that of the first layer, where a crystalline-like L-TA phase was found as a predominant component. Our results imply a preferential crystalline growth of chiral molecules on the same chiral surface, which may lead to a work for optical resolution into two enantiomers at a solid-liquid interface.

Original languageEnglish
Pages (from-to)1772-1778
Number of pages7
JournalJournal of Nanoscience and Nanotechnology
Volume6
Issue number6
DOIs
Publication statusPublished - 2006 Jun
Externally publishedYes

Keywords

  • Chiral Surface
  • Fourier Transform Infrared-Reflection Adsorption Spectroscopy
  • Gemini (Dimeric) Surfactant
  • Molecular Recognition
  • Quaternary Ammonium
  • Self-Assembled Monolayer
  • Surface Plasmon Rasonance

ASJC Scopus subject areas

  • Bioengineering
  • Chemistry(all)
  • Biomedical Engineering
  • Materials Science(all)
  • Condensed Matter Physics

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