The anion binding features of pyrrole- and benzene-strapped calix[4]pyrroles 1 and 2, in particular, for F– and HCO3– have been examined by means of NMR spectroscopy in DMSO-d6, CDCl3, and CD3CN, respectively. Receptors 1 and 2 were found to bind F– and HCO3– tightly via slow binding/release equilibria in these solvents. A combination of 1H and 19F NMR spectroscopic analyses with mass spectrometry revealed that contacting calix[4]pyrroles 1 and 2 with F– and HCO3– salts prompts deuterium exchange of the NH protons in the three nominally aprotic deuterated solvents considered in this study.

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