To understand the influence of molecular shape on the optoelectronic properties of heteroacenes, we report here the syntheses and characterizations of two linear- and two arch-shaped dibenzothienopyrrole (DBTP) derivatives, namely, N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole (l-HDBTP), N-phenyldibenzothieno[3,2-b:2′,3′-d]pyrrole (l-PDBTP), N-hexyldibenzothieno[2,3-b:3′,2′-d]pyrrole (a-HDBTP) and N-phenyldibenzothieno[2,3-b:3′,2′-d]pyrrole (a-PDBTP). Their structure-property relationships have been systematically studied by optical absorption, cyclic voltammetry, single-crystal X-ray diffraction analyses and the single-crystal-based and thin-film-based field-effect transistors (FETs). The results demonstrate that the arch-shaped DBTP derivatives can modify their electronic structures and molecular arrangements by tuning of substituents, to obtain a better charge-transporting ability relative to the linear-shaped ones. The arch-shaped N-phenyl substituted a-PDBTP exhibits optimum molecular π-stacking arrangement and charge transport properties, with the hole mobility of 0.75 cm²V⁻¹s⁻¹ and 0.058 cm²V⁻¹s⁻¹ for the single-crystal and the thin-film OFETs, respectively. These results indicate that the arch-shaped DBTP core is a promising building block in the area of organic semiconducting materials.

为了了解分子形状对杂苯乙炔光电性能的影响，我们在这里报告了两个线性和两个弓形的二苯并噻吩并吡咯（DBTP）衍生物，即N-己基二苯并噻吩并[3,2- b：2' ，3'- d ]吡咯（1- HDBTP），N-苯基二苯并噻吩并[3,2- b：2'，3'- d ]吡咯（1- PDBTP），N-己基二苯并噻吩并[2,3- b：3' -1,2'- d ]吡咯（一个-HDBTP）和ñ-苯基二苯并噻吩并[2,3- b：3'，2'- d ]吡咯（a- PDBTP）。通过光吸收，循环伏安法，单晶X射线衍射分析以及基于单晶和薄膜的场效应晶体管（FET），系统地研究了它们的结构-特性关系。结果表明，弓形DBTP衍生物可以通过取代基的调节来改变其电子结构和分子排列，从而获得相对于线性形的更好的电荷传输能力。拱形的N-苯基取代了-PDBTP具有最佳的分子π堆积排列和电荷传输性能，对于单晶和薄膜OFET，空穴迁移率分别为0.75 cm ² V ^-1 s ^-1和0.058 cm ² V ^-1 s ^-1。这些结果表明，拱形DBTP芯是有机半导体材料领域中一个有前途的构建基块。