Selenophene-Based Heteroacenes: Synthesis, Structures, and Physicochemical Behaviors

On
the basis of three new building blocks, dithieno­[3,2-b:2′,3′-d]­selenophene (tt-DTS), diseleno­[3,2-b:2′,3′-d]­thiophene (tt-DST), and
diseleno­[3,2-b:2′,3′-d]­selenophene (tt-DSS), four thiophene-
and selenophene-based heteroacenes (3a–d) with up to seven fused rings were designed and synthesized. Another
two selenophene-based heteroacenes (1 and 2) with three and five fused rings were prepared. The molecular structures
of 1, 2, 3a, and 3c were confirmed by single-crystal analysis. The results showed that
molecular structures, spectroscopy features, and cyclic voltammetry
behaviors could be modulated by changing the heteroatoms from sulfur
to selenium for 3a–d or changing
the numbers of selenophene rings for 1, 2, and 3d.