Synthesis and molecular properties of tricyclic biselenophene-based derivatives with nitrogen, silicon, germanium, vinylidene, and ethylene bridges

A new class of biselenophene-based materials including an sp³-silicon-bridged diselenosilole (DSS), an sp³-germanium-bridged diselenogermole (DSG), and an sp³-nitrogen-bridged diselenopyrrole (DSP) as well as an sp²-vinylidene-bridged dicyanodiselenofulvene (CDSF), a diacetylenediselenofulvene (ADSF), and a dioctylethylene-bridged benzodiselenophene (BDS) have been successfully synthesized and characterized. The bridging moieties play an important role in determining the optical and electrochemical properties. The six brominated derivatives are ready to construct various biselenophene-based conjugated materials with tunable properties for organic photovoltaics and field effect transistors.