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Synthetic supramolecular receptors have been widely used to study reversible solution binding of anions; however, few systems target highly-reactive species. In particular, the hydrochalcogenide anions hydrosulfide (HS - ) and hydroselenide (HSe - ) have been largely overlooked despite their critical roles in biological systems. Herein we present the first example of reversible HSe - binding in two distinct synthetic supramolecular receptors, using hydrogen bonds from N-H and aromatic C-H moieties. The arylethynyl bisurea scaffold 1  t   Bu  achieved a binding affinity of 460 ± 50 M -1 for HSe - in 10% DMSO- d  6 /CD 3 CN, whereas the tripodal-based receptor 2 CF 3   achieved a binding affinity of 290 ± 50 M -1 in CD 3 CN. Association constants were also measured for HS - , Cl - , and Br - , and both receptors favored binding of smaller, more basic anions. These studies contribute to a better understanding of chalcogenide hydrogen bonding and provide insights into further development of probes for the reversible binding, and potential quantification, of HSe - and HS - .

Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSe−) anion

Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSe⁻) anion