Development of a Synthetic Supramolecular Receptor for the Hydrosulfide Anion

Abstract

Hydrogen sulfide (H2S) has recently emerged as an important biomolecule in cellular signaling. As its significance in various physiological processes in the cardiovascular, digestive, nervous, and immune systems is still being uncovered, reversible detection techniques for H2S and its predominant form, hydrosulfide (HS–), are necessary to properly research the binding and activity of this gasotransmitter. This thesis reports the first synthetic receptor capable of reversibly binding HS–. In addition to hydrogen bonding from urea NH groups to HS–, this receptor also uses a notable aromatic CH---S hydrogen bond to achieve binding constants of up to 90,300 ± 8700 M–1 in acetonitrile. This fundamental study should pioneer work toward developing new, synthetic HS– receptors and increase the understanding of biological HS– receptors and synthetic H2S recognition techniques.