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Science 2 September 1994:
Vol. 265. no. 5177, pp. 1413 - 1415
DOI: 10.1126/science.265.5177.1413
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Articles

Molecular Recognition by Self-Assembled Monolayers of Cavitand Receptors

K. D. Schierbaum 1, T. Weiss 1, E. U. Thoden van Veizen 2, J. F. J. Engbersen 2, D. N. Reinhoudt 2, and W. Göpel 1

1 Institute of Physical and Theoretical Chemistry, University of Tübingen, Auf der Morgenstelle 8, D-72076-Tübingen, Germany
2 Department of Organic Chemistry, MESA Research Institute, Post Office Box 217, 7500 AE Enschede, Netherlands

It is shown by angle-resolved x-ray photoelectron spectroscopy that cavitands derived from resorcin[4]arenes provided with four dialkylsulfide chains form stable monolayers on gold surfaces that are well organized by self-assembly. The cavitand headgroups at the surface of the resorcin[4]arene monolayer act as molecular recognition sites for small organic molecules with remarkable selectivity for perchloroethylene (C2Cl4). Comparative thermal desorption experiments indicate binding sites with high interaction energies of C2Cl4 at the surface of the resorcin[4]arene monolayers. Fast and reversible "host-guest" interactions were found by the monitoring of extremely small mass changes (in the nanogram range) with a quartz microbalance oscillator provided with gold electrodes coated by resorcin[4]arene monolayers.

Submitted on March 14, 1994
Accepted on June 21, 1994


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Polycaps: Reversibly formed polymeric capsules.
R. K. Castellano, D. M. Rudkevich, and J. Rebek Jr. (1997)
PNAS 94, 7132-7137
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