Given the biological importance of organic cations, the facilitated transport of organic ion pairs could find many applications. Calix[6]arene tris(thio)ureas, which possess a cavity that can accommodate primary ammonium ions, can not only act as carriers for Cl /NO antiport but can also perform the cotransport of PrNH Cl. Transport was monitored by fluorescence spectroscopy and the presence of the different species inside the vesicles was characterized by H and Cl NMR experiments involving shift reagents. The cotransport of PrNH Cl was also observed by receptors deprived of a cavity, but the presence of the cavity conveys an advantage, as the cotransport by calix[6]arenes was observed to be more efficient than the Cl /NO antiport, which is not the case with receptors without a cavity. The role played by the cavity was further highlighted by the disappearance of this advantage when using a bulky ammonium ion, which cannot be complexed within the cavity.
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