We present a new class of diketopyrrolopyrrole (DPP) derivatives, which comprise the ethenylidene linker that connects the DPP unit to aryls, such as thiophene (TE-DPP), furan (FE-DPP), and cyanothiophene (CNTE-DPP), respectively. The introduction of ethenylidene linkers led to extended π-conjugation length and enhanced intramolecular charge transfer, giving rise to prominent red shift in the visible region of the spectrum, low-lying lowest unoccupied molecular orbital (LUMO) level, and the narrow band gap. The single-crystal X-ray diffraction analysis reveals that the resulting compounds exhibit planar configurations with close π–π distances of 3.17 Å. Furthermore, these compounds exhibit one-dimensional arrangement, which benefits from intramolecular and intermolecular hydrogen bonds, facilitating short contact between donor and acceptor segments. Organic field-effect transistor (OFET) measurements reveal that TE-DPP and FE-DPP exhibit p-type transport behavior with maximum mobility of 0.05 and 0.18 cm² V^–1 s^–1, respectively. While CNTE-DPP exhibits ambipolar transport characteristics with electron and hole mobilities up to 0.13 and 0.24 cm² V^–1 s^–1, respectively. Our work demonstrates the potential of aryl-ethenyl-substituted diketopyrrolopyrroles (ArE-DPPs) as promising semiconducting materials for applications in organic electronic devices.

中文翻译：

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具有反式构型和超近π平面堆叠距离的芳基乙烯基取代二酮吡咯并吡咯半导体

我们提出了一类新的二酮吡咯并吡咯 (DPP) 衍生物，其包含将 DPP 单元连接到芳基的亚乙烯基连接基，例如分别为噻吩 ( TE-DPP )、呋喃 ( FE-DPP ) 和氰基噻吩 ( CNTE-DPP ) 。亚乙烯基连接体的引入导致了π共轭长度的延长和分子内电荷转移的增强，从而在光谱的可见光区域产生了显着的红移、低位最低未占分子轨道（LUMO）能级和窄带隙。单晶 X 射线衍射分析表明，所得化合物呈现出 π-π 距离为 3.17 Å 的平面构型。此外，这些化合物表现出一维排列，这得益于分子内和分子间氢键，促进供体和受体片段之间的短接触。有机场效应晶体管 (OFET) 测量表明，TE-DPP和FE-DPP表现出 p 型输运行为，最大迁移率分别为 0.05 和 0.18 cm ² V ^–1 s ^–1。而CNTE-DPP表现出双极输运特性，电子和空穴迁移率分别高达0.13和0.24 cm ² V ^–1 s ^–1。我们的工作证明了芳基乙烯基取代的二酮吡咯并吡咯（ ArE-DPP）作为有机电子器件应用的有前景的半导体材料的潜力。