Synthesis and Characterization of Dibenzodioxadiselenafulvalene

Dibenzodioxadiselenafulvalene (DBOSF) was prepared and the cis and trans isomers were separated. X-ray crystallographic analysis revealed the presence of Se- - -H and O- - -H hydrogen bonds in both crystals. The electrochemical properties of cis- and trans-DBOSFs together with dibenzotetraoxafulvalene (DBTOF) and cis- and trans-dibenzodioxadithiafulvalenes were investigated by means of cyclic voltammetry and DFT calculation. The electron-donating ability and the stability of oxidized forms of DBOSFs are improved compared with those of DBTOF.