Halogen-bond-based cooperative ion-pair recognition by a crown-ether-embedded 5-iodo-1,2,3-triazole

A crown-ether containing the iodo-triazole moiety for simultaneous cation–anion binding through Lewis-basic nitrogen atoms and C–I⋯I halogen-bond-donating iodine atoms was prepared. The complexation of the heteroditopic receptor was illustrated by X-ray and DFT analysis. The cooperative effect boosting the anion affinity was quantified by 1H/13C NMR titration experiments.