Easily Reducible Materials from the Reactions of Diselenopheno[3,2-b:2 ',3 '-d]pyrrole and Dithieno[3,2-b:2 ',3 '-d]pyrrole with Tetracyanoethylene

Abstract

A new core, 4H-diselenopheno[3,2-b:2′,3′-d]pyrrole (DSP), was reacted with tetracyanoethylene, and three products, mono-tricyanovinyl, bis-tricyanovinyl, and quinoidal, were isolated and compared with the respective 4H-dithieno[3,2-b:2′,3′-d]pyrrole (DTP) derivatives using cyclic voltammetry, UV–vis absorption, and differential scanning calorimetry analyses. Organic field-effect transistors were fabricated using solution-processed films, and only one derivative, bis-tricyanovinyl-DSP, exhibited transistor behavior with μe reaching 8.7 × 10–4 cm2/V·s. This enhancement of the electron-transporting properties in comparison with DTP derivative is attributed to stronger LUMO–LUMO interaction due to a larger size of selenium atom, which in the case of the bis-tricyanovinyl derivative, has wave function density on the chalcogen.