Synthesis and Anion Binding Assessment of Novel Adamantane Amidopyrroles

Abstract

Two new adamantane anion receptors with amidopyrrole side arms were prepared and their anion binding ability in DMSO solutions with TBA salts (Cl–, AcO– and H2PO4–) was investigated by UV/Vis spectroscopy. After calculating the corresponding association constants of receptor-anion complexes, it became apparent that only one amidopyrrole side arm was engaged in complexation. These experimental findings were rationalized using computational tools and the binding mode was proposed. In addition to the found 1 : 1 stoichiometry, we showed that the studied receptors bind oxo-anions (H2PO4– and AcO–) more strongly than spherical halogenide (Cl–) anions.