Diketopyrrolopyrrole (DPP), typically flanked with thiophene rings as π-spacers, has been regarded as a promising electron-acceptor unit for constructing donor-acceptor-donor (D-A-D) type small molecule organic semiconductors. Exploring the relationships between its conjugation structure and semiconducting property is of great importance for both molecular design and device fabrication of such DPP materials. Herein we describe the synthesis, self-assembly, and transistor characteristics of two novel N- and N′− 2-octyldodecylated DPP derivatives which were modified with native anthracene (An) and brominated anthracene (Br-An) at 5-, 5′-position of the flanked thiophenes, respectively, namely An-DPP and Br-An-DPP. Attributing to the self-assembly behaviors, they exhibit enormous difference in hole transport characteristics on interdigitated-electrode based organic field-effect transistor (OFET) devices even though there is only two atoms’ discrepancy in accordance with their molecular structures. The characterization of OFETs with interdigitated-electrodes based on Br-An-DPP reveals p-channel operation with highest field-effect mobility of 0.2 cm²·V⁻¹·s⁻¹, which is 10⁷ times higher than that of An-DPP (4.8 × 10⁻⁸ cm²·V⁻¹·s⁻¹), and with a threshold voltage of - 2.5 V. X-ray diffraction, atomic force microscopy, scanning electron microscopy, and optical absorption studies reveal the presence of crystalline films caused by bromination on anthracene-modified alkylated DPP (i.e., Br-An-DPP), while An-DPP exhibits completely amorphous phase.

吡咯并吡咯二酮（DPP）通常两侧带有噻吩环作为π-间隔物，被认为是构建供体-受体-供体（DAD）型小分子有机半导体的有前途的电子受体单元。探索其共轭结构与半导体特性之间的关系对于此类 DPP 材料的分子设计和器件制造都具有重要意义。在这里，我们描述了两种新型 N- 和 N'- 2-辛基十二烷基化 DPP 衍生物的合成、自组装和晶体管特性，这些衍生物在 5-、5' 处用天然蒽 ( An ) 和溴化蒽(Br-An)修饰- 侧翼噻吩的位置，分别为An-DPP和Br-An-DPP. 由于自组装行为，它们在基于叉指电极的有机场效应晶体管 (OFET) 器件上的空穴传输特性表现出巨大差异，尽管它们的分子结构只有两个原子的差异。基于Br-An-DPP的具有叉指电极的 OFET 的表征揭示了具有最高场效应迁移率 0.2 cm ² ·V ^-1 ·s ^-1的 p 沟道操作，比An -高10 ^7倍DPP (4.8 × 10 ^-8 cm ² ·V ^-1 ·s ^-1)，并且阈值电压为 - 2.5 V。X 射线衍射、原子力显微镜、扫描电子显微镜和光学吸收研究揭示了由溴化引起的在蒽改性烷基化 DPP（即Br-An -DPP )，而An-DPP表现出完全非晶相。