Electroactive C-2 symmetry receptors based on the biphenyl scaffold and tetrathiafulvalene units

摘要

The synthesis of a family of biphenyl-tetrathiafulvalene ( TTF) derivatives incorporating a binding site has been carried out in good to moderate yields through functionalization of the biphenyl scaffold. X-ray structure of one derivative ( compound 3) of the series is provided and shows a dihedral angle of 74 around the central Ar-Ar bond of the biphenyl unit in a cisoid conformation. H-1 NMR and cyclic-voltammetry studies demonstrate the critical importance of the nature of the substitution on the conformational rigidity and on the electrochemical behavior of the resulting biphenyl-TTF assemblies. This feature is underlined by an original electrochemical recognition process upon binding of Pb2+, correlated to conformational changes occurring upon metal cation complexation.