Syntheses, electrochemical behaviors, spectral properties and DFT calculations of two 1,3-dithiole derivatives

Abstract

Two new 1,3-dithiole derivatives, 4,4′-{9-[4,5-bis(methylthio)-1,3-dithiol-2-ylidene]-9H-fluorene-2,7-diyl} dipyridine(2a) and 3,3′-{9-[4,5-bis(methylthio)-1,3-dithiol-2-ylidene]-9H-fluorene-2,7-diyl} dipyridine(2b) were synthesized and characterized by Fourier transform infrared(FTIR), ¹H NMR, ¹³C NMR and mass spectroscopies. The crystal structure of compound 2b was also studied. The optimized conformations and molecular orbital diagrams of compounds 2a and 2b were illustrated via density functional theory(DFT). By the time-dependent DFT(TD-DFT) method, electronic absorption spectra of compounds 2a and 2b were predicted and the results achieved were in good agreement with the experimental data. The formation of the cationic radical during the electrochemical oxidation process was also proposed.

Keywords

1,3-Dithiole derivative / Pyridine / X-Ray diffraction / Linear sweep voltammetry / Density functional theory(DFT) calculation

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