Benzo[c][1,2,5]selenadiazole organoselenium derivatives: Synthesis, X-ray, DFT, Fukui analysis and electrochemical behavior

Organo-selenium compounds are of a broad spectrum of potential technical applications. To date, many efforts have been devoted to develop their chemistry. In this context, two benzo[c][1,2,5]selenadiazole compounds have been synthesized and characterized by 1H NMR, 13C NMR, 19F NMR, MS and UV–Vis spectroscopic techniques. Both structures were confirmed using single-crystal X-ray diffraction analysis. Each compound crystallizes in monoclinic systems, space group P21/c forming dimeric units due to the intermolecular Se⋯N interactions. The dimmers are further linked by weak π···π stacking interactions between 1,2,5-selenadiazole and the six-membered aromatic rings. The electrochemical behavior of the compounds has been investigated by cyclic voltammetry. Additionally, the structural geometrical parameters, vibrational, electronic transition, Fukui analysis and redox properties of the molecules have been rationalized by DFT and TD-DFT methods using B3LYP level of theory in conjunction with 6-311G(d,p) basis set implemented in Gaussian 09 program. As a result, an excellent correlation between the electronic transitions and the electrochemical behavior was found.