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.

以三种新型构筑单元——二噻吩并[3,2-b:2′,3′-d]硒吩（dithieno[3,2-b:2′,3′-d]selenophene，tt-DTS）、二硒吩并[3,2-b:2′,3′-d]噻吩（diseleno[3,2-b:2′,3′-d]thiophene，tt-DST）以及二硒吩并[3,2-b:2′,3′-d]硒吩（diseleno[3,2-b:2′,3′-d]selenophene，tt-DSS）——为基础，本研究设计并合成了4种含至多7个稠环的噻吩与硒吩基杂并苯类化合物（3a~d）。此外，还制备了另外2种分别包含3个和5个稠环的硒吩基杂并苯类化合物（1和2）。通过单晶结构分析确证了化合物1、2、3a及3c的分子结构。研究结果表明，对于3a~d系列化合物，可通过将杂原子从硫替换为硒；对于1、2与3d，则可通过调整硒吩环的数目，来调控其分子结构、光谱特性以及循环伏安行为。