(Thio)urea Resorcinarene Cavitands. Complexation and Membrane Transport of Halide Anions
Autor: | J. Willem M. Nissink, Willem Verboom, Harold Boerrigter, Lennart Grave, David N. Reinhoudt, John H. van der Maas, Feike de Jong, Lysander A. J. Chrisstoffels |
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Přispěvatelé: | Faculty of Science and Technology, Molecular Nanofabrication |
Rok vydání: | 1998 |
Předmět: | |
Zdroj: | Journal of organic chemistry, 63(13), 4174-4180. American Chemical Society |
ISSN: | 1520-6904 0022-3263 |
Popis: | Reaction of aminomethylcavitands with iso(thio)cyanates gives (thio)urea-functionalized resorcinarene cavitands, which represent a novel class of neutral anion receptors. The complexation of halide anions has been studied both with infrared and 1H NMR spectroscopy. The receptors have a small preference for chloride over the other halides; p-fluorophenylthiourea cavitand 8a gives the highest association constant (Kass = 4.7 × 105 M-1 with chloride in CDCl3). A cooperative effect of the ligating (thio)urea moieties is indicated by the lower affinity of the corresponding tris(thio)urea-functionalized cavitands. For the first time facilitated membrane transport of halide anions through supported liquid membranes is achieved. |
Databáze: | OpenAIRE |
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