Enantioselective adsorption of surfactants monitored by ATR-FTIR
The selectivity of adsorption of chiral surfactants to a chiral monolayer at the solid-liquid interface was studied using attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR). One enantiomer of the chiral surfactant was deuterated, which causes a change in the IR absorption...
| Veröffentlicht in: | Langmuir : the ACS journal of surfaces and colloids. - 1991. - 26(2010), 17 vom: 07. Sept., Seite 13944-53 |
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| Weitere Verfasser: | , |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2010
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| Zugriff auf das übergeordnete Werk: | Langmuir : the ACS journal of surfaces and colloids |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't Amino Acids Membranes, Artificial Surface-Active Agents Silicon Z4152N8IUI |
| Zusammenfassung: | The selectivity of adsorption of chiral surfactants to a chiral monolayer at the solid-liquid interface was studied using attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR). One enantiomer of the chiral surfactant was deuterated, which causes a change in the IR absorption frequency, and allows independent measurement of the adsorption of each molecule. Both the surfactant, N-lauroyl phenylalanine (NLP), and the chiral monolayer, N-L-phenylalaninoyl, 11-undecyl-silicon, were amino acid derivatives. An enantiomeric excess of 56 +/- 22% of the L over D was observed for adsorption to the interface between a carbon tetrachloride solution containing a quasi-racemate of N-lauroyl phenylalanine and the N-L-phenylalaninoyl, 11-undecyl monolayer film on silicon. In contrast, equimolar adsorption occurred from an equimolar mixture of hydrogenated and deuterated forms of the L surfactant. The measured enantiomeric excess strongly depended on the density of chiral surface groups: the higher the density of chiral groups on the surface, the better the enantiodiscrimination, even though the total adsorption was roughly constant. This nonlinear behavior indicates that more than one chiral surface group is required for significant selectivity |
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| Beschreibung: | Date Completed 27.12.2010 Date Revised 21.11.2013 published: Print Citation Status MEDLINE |
| ISSN: | 1520-5827 |
| DOI: | 10.1021/la101641r |