The creation of receptors that can bind ion pairs may afford unique selectivities that can be exploited in the sensing and extraction of salts in biology and chemistry. Compared to the large number of cation and anion receptors that have been developed over the past decades, the examples of synthetic molecules that can selectively bind these ions as pairs are not common. To explore this area, a triazole-based macrocyclic ion pair receptor has been designed and synthesized. The Janus-type macrocycle has both hydrogen bond donors and acceptors that can face into the cavity's center. It has been found that the macrocycle binds the sodium perchlorate ion pair in a mixture of CD2Cl2 and CD3CN as a 1:1:1 complex with an apparent association constant that exceeds those observed for the perchlorate anion or sodium cation alone. It is believed that the contact between the ion pairs in the complex's cavity serves as the driving force for the putative cooperativity. Progress towards characterizing the binding mode and the ion pair selectivity will be presented.

Aryl-triazole derived Janus macrocycle as ion pair receptor

246th National Meeting (2013)

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