(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions

Harold Boerrigter, Lennart Grave, J. Willem M. Nissink, Lysander A.J. Chrisstoffels, John H. van der Maas, Willem Verboom, Feike de Jong, David N. Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

72 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)4174-4180
JournalJournal of organic chemistry
Volume63
Issue number13
DOIs
Publication statusPublished - 1998

Fingerprint Dive into the research topics of '(Thio)urea resorcinarene cavitands: Complexation and membrane transport of halide anions'. Together they form a unique fingerprint.

Cite this