The pyridazine–tetrathiafulvalene conjugates: synthesis, photophysical, and electrochemical properties

To study the electronic interactions in donor–acceptor (D–A) conjugates as a precursor of optoelectronic materials, a series monopyridazine-annulated tetrathiafulvalenes and a bispyridazine-annulated tetrathiafluvalene were synthesized by a condensation reaction of 2,3-dimethoxycarbonyl-6,7-dibutylthiotetrathiafulvalene or/and 2,3,6,7-tetramethoxycarbonyltetrathiafulvalene with hydrazine hydrate and structurally characterized by conventional chemical and physical methods. Their electronic properties have been studied experimentally by the combination of electrochemistry and UV–vis spectroscopy. All of monopyridazine-tetrathiafulvalene conjugates 7–13 show intramolecular charge transfer interaction in ground states, which is rationalized on the basis of density functional theory. Their HOMO energy levels and Egopt values were estimated to be −4.88 to −5.07 eV from cyclic voltammetry and 2.43–2.79 eV from the absorption spectra, respectively. The X-ray crystallographic analyses of the pyridazine–tetrathiafulvalene conjugates 7, 11–13 are also reported.

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