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.

本研究以三种新型结构基元——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，设计并合成了4种基于噻吩与硒吩的稠环杂芳烃（3a~d），其稠合环数目最高可达7个。此外，还制备了另外2种基于硒吩的稠环杂芳烃（1和2），分别含有3个和5个稠合环。通过单晶结构分析确认了化合物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，将杂原子由硫替换为硒，或是针对1、2及3d系列调整硒吩环的数目，均可对其分子结构、光谱特性以及循环伏安行为进行调控。