Electroactive C(2) symmetry receptors based on the biphenyl scaffold and tetrathiafulvalene units.
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 degrees around the central Ar-Ar bond of the biphenyl unit in a cisoid conformation. (1)H 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 Pb(2+), correlated to conformational changes occurring upon metal cation complexation.
Delogu
Giovanna
G
Istituto CNR di Chimica Biomolecolare, Traversa La Crucca, 3, I-07040 Sassari, Italy. giovanna.delogu@icb.cnr.it
Fabbri
Davide
D
Dettori
Maria Antonietta
MA
Sallé
Marc
M
Derf
Franck Le
FL
Blesa
Maria-Jesus
MJ
Allain
Magali
M
D001713:Biphenyl Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004563:Electrochemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D021241:Spectrometry, Mass, Electrospray Ionization
D001713:Biphenyl Compounds; D006571:Heterocyclic Compounds; C063887:tetrathiafulvalene