Abstract
We present the synthesis and structure characterization of three novel symmetrical azomethines 3a-c derived from 2,5-diamino-thiophene-3,4-dicarbonitrile together with the unexpected by-product 4 containing the saturated hemiaminal type bond. Photophysical properties (UV–Vis and photoluminiscence) are shown to be affected mainly by the central thiophene unit with no influence from the type of linkage – unsaturated imine (-HCN-) bond in 3a-cvs. the saturated hydroxymethylamino circuit [–HN–C(OH)H-] in 4. For the first time the electronic properties, such as distribution of the frontier molecular orbitals and resulting energy gaps, for compounds 3b,c and 4 are calculated by means of density functional theory methods and confirmed by an immediate experimental method - the energy-resolved electrochemical impedance spectroscopy.
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