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À propos de : Synthesis, Spectroscopic, Electrochemical and Pb2+-Binding Studiesof Tetrathiafulvalene Acetylene Derivatives        

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  • Synthesis, Spectroscopic, Electrochemical and Pb2+-Binding Studiesof Tetrathiafulvalene Acetylene Derivatives
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  • A series of tetrathiafulvalene acetylene derivatives, [TTF−C⋮C−A] [A = C6H4N(CH3)2-4 (1), C6H4OCH3-4 (2), C6H5 (3), C6H4F-4 (4), C6H4NO2-4 (5), C5H4N-2 (6), C5H4N-3 (7), and C5H4N-4 (8)], havebeen designed and synthesized to provide insight into the nature of the donor−acceptor interaction viaa π-conjugated triple bond. The X-ray crystal structure of [TTF−(C⋮C)−C6H4OCH3-4] (2) reveals thatthe phenyl ring linked by acetylene is almost coplanar to the plane of TTF with a dihedral angle of 3.6°.The strong intermolecular C−H···O hydrogen bonding was found to direct the molecular helical assemblieswith a screw pitch of 5.148 Å when viewed along the a-axis. Spectroscopic and electrochemical behaviorsof the tetrathiafulvalene acetylene derivatives demonstrate that the TTF unit interacts with the electron-accepting group through the triple bond, thus leading to the intramolecular charge transfer. The pyridine-substituted TTF compounds 6−8 show remarkable sensing and coordinating properties toward Pb2+.Comparison of the spectroscopic and electrochemical properties and the calculation at the B3LYP/6-31G* level available in Gaussian 03 reveals that varying the bridged unit of the TTF-π-A system froma double bond to a triple bond leads to positive shifts for the first and second oxidation potentials of theTTF moieties, while the extent of intramolecular charge transfer interactions through the π-conjugatedtriple bond is smaller than that through the double bond.
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