Molecular Recognition by Self-Assembled Monolayers of Cavitand Receptors

• Published in: Science (American Association for the Advancement of Science) Vol. 265; no. 5177; pp. 1413 - 1415
• Main Authors: Schierbaum, K. D., Weiss, T., E. U. Thoden van Velzen, Engbersen, J. F. J., Reinhoudt, D. N., Göpel, W.
• Format: Journal Article
• Language: English
• Published: Washington, DC American Society for the Advancement of Science 02-09-1994; American Association for the Advancement of Science
• Subjects: Atoms; Binding energy; Chemistry; Desorption; Electrons; Exact sciences and technology; General and physical chemistry; Low temperature; Molecular biology; Molecular interactions; Molecules; Monomolecular films; Oscillators; Receptors; Solid-liquid interface; Surface physical chemistry; Vapor phases; Monolayer; Gold; Liquid solid interface; Molecular structure; Metallic adsorbent; Transition metal; Oxygen heterocycle; Recognition; Macrocycle
• ISSN: 0036-8075; 1095-9203
• DOI: 10.1126/science.265.5177.1413

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 (C$_2$Cl$_4$). Comparative thermal desorption experiments indicate binding sites with high interaction energies of C$_2$Cl$_4$ 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.