Formation of Chiral Interdigitated Multilayers at the Air-Liquid Interface Through Acid-Base Interactions-Reference-Cited by-全球学者库

Formation of Chiral Interdigitated Multilayers at the Air-Liquid Interface Through Acid-Base Interactions

Published:1996-12-20 Issue:5295 Volume:274 Page:2046-2049
ISSN:0036-8075
Container-title:Science
language:en
Short-container-title:Science

Author:

Kuzmenko Ivan¹,Buller Ronith¹,Bouwman Wim G.²,Kjær Kristian²,Als-Nielsen Jens³,Lahav Meir¹,Leiserowitz Leslie¹

Affiliation:

1. I. Kuzmenko, R. Buller, M. Lahav, L. Leiserowitz, Department of Materials and Interfaces, Weizmann Institute of Science, Rehovot 76100, Israel.

2. W. G. Bouwman and K. Kjær, Department of Solid State Physics, Risø National Laboratory, DK-4000 Roskilde, Denmark.

3. J. Als-Nielsen, Niels Bohr Institute, H. C. Ørsted Laboratory, DK-2100 Copenhagen, Denmark.

Abstract

Thin interdigitated films composed of a long-chain, water-insoluble chiral acid (p -pentadecylmandelic acid of absolute configuration R ) and a water-soluble chiral base (phenylethylamine, R′ ) were constructed at the air-solution interface. The ( R, R′ ) structure was characterized to near-atomic resolution by grazing-incidence x-ray diffraction (GIXD). The two diastereomeric systems, ( R, R′ ) and ( R, S′ ), demonstrate similar surface pressure-molecular area isotherms, but their structures are completely different on the molecular level, as monitored by GIXD. Complementary data on these two architectures were provided by atomic force microscopy.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference19 articles.

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2. Brianso M. C., Leclercq M., Jacques J., Acta Crystallogr. B35, 2751 (1979).

3. Larsen S., Diego H. L., ibid. B49, 303 (1993).

4. We synthesized ( R )- p -pentadecylmandelic acid by the Friedel-Craft reaction of pentadecyl benzene with oxalyl chloride in chloroform at 0° to 5°C to yield the α-keto acid [O. Itoh et al . Bull. Chem. Soc. Jpn. 57 810 (1984)]. The latter was esterified to the corresponding methoxy ester and subsequently reduced by the NaBH 4 ( R R )tartaric acid complex according to the method of H. Iwagami et al. [ ibid. 64 175 (1991)] to yield ( R )- p -pentadecyl methyl mandelate with an enantiomeric excess (ee) of 57%. We determined this value by nuclear magnetic resonance (NMR) analysis using the tris [3-(trifluoromethylhydroxymethylene)-(+)camphorato]europium(III) complex. The compound was hydrolyzed to the corresponding acid and then the optical purity was enhanced up to 97% ee by cocrystallization with commercially available R -PEA. The optical purity was checked by NMR and circular dichroism spectra: [α] D 25 = −63.2 (C = 1.01 g/liter tetrahydrofuran).

5. The isotherms were measured from A = 100 to 5 Å 2 per molecule.

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