Recognition Properties of an Acyclic Biphenyl-Based Receptor toward Carbohydrates

Biphenyl-based receptor 1, incorporating four heterocyclic recognition units, was synthesized, and its binding properties toward neutral sugars were determined. Receptor 1 is a representative of a new series of acyclic carbohydrate-binding receptors, which were designed to recognize disaccharides. The compound 1 has been established as a highly effective receptor for dodecyl β-d-maltoside, showing successive 1:1 and 2:1 receptor/substrate complexation behavior toward the disaccharide. Both hydrogen bonding and interactions of the sugar CH's with the aromatic units of the receptor contribute to the stabilization of the receptor−maltoside complexes.