Anion recognition by a family of quinoline-functionalised bis-amide hosts in solid state and in solution

Abstract

The interaction between a series of bidentate, amide-functionalised 8-oxyquinoline receptors and coordinating anions is investigated. Anion recognition properties and conformations were studied by solid-state structures, Hartree–Fock calculations and solution-phase 1H NMR investigations. Our findings suggest that the amide-oxyquinoline motif coordinates anions and water with a well-defined, consistent geometry involving multiple hydrogen bonds. Solution studies of the neutral receptors reveal the unprotonated oxyquinoline ring to indirectly contribute to anion binding by the adjacent amide NH groups despite being unable to directly participate through hydrogen bonding.