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Hepta‐thienoacenes with Internal Carbazole: Synthesis, Regioselectivities and Organic Field‐Effect Transistor Applications
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-08-21 , DOI: 10.1002/ajoc.201800368 Yueming Hu 1 , Hao Wang 1 , Shuli Liu 1 , Jing Zhang 1 , Baomin Zhao 1 , Nina Fu 1 , Mingdong Yi 1 , Wei Huang 1, 2
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-08-21 , DOI: 10.1002/ajoc.201800368 Yueming Hu 1 , Hao Wang 1 , Shuli Liu 1 , Jing Zhang 1 , Baomin Zhao 1 , Nina Fu 1 , Mingdong Yi 1 , Wei Huang 1, 2
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Acenes/heteroacenes, the most widely studied small‐molecule organic semiconductors, always possess linear structures. In this work, three stable, soluble and angular π‐extended hepta‐thienoacenes with an internal carbazole, that is, thienobenzo‐fused carbazole (DTBCz) were synthesized via a four‐step tandem method. The tandem synthesis starting from carbazole derivatives led to interesting isomeric effects. The synthetic regioselectivity was discussed in detail. Their physical properties and electron density distributions were studied by UV/Vis absorption, photoluminescence, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltammetry (CV) measurements, and theoretical calculations. Their potentials as semiconducting materials were evaluated by fabricating the solution‐processed organic field‐effect transistors (OFETs). The more angular shaped isomer of DTB[32,34]Cz displayed the best performance with hole mobility up to 0.0044 cm2 V−1 s−1 in devices with a thickness of ca. 115 nm. Particularly, the performance of DTB[32,34]Cz‐based devices showed less dependence on the thickness of their active layer.
中文翻译：
七噻吩并蒽与内部咔唑的合成，区域选择性和有机场效应晶体管应用
并苯/杂并苯是研究最广泛的小分子有机半导体，始终具有线性结构。在这项工作中，三个稳定的，可溶的且呈角π扩展的七噻吩并并庚酮与内部咔唑，即噻吩并苯并稠合的咔唑（DTBCz）是通过四步串联方法合成的。从咔唑衍生物开始的串联合成导致有趣的异构体效应。合成区域选择性进行了详细讨论。通过紫外/可见吸收，光致发光，热重分析（TGA），差示扫描量热法（DSC），循环伏安法（CV）测量和理论计算研究了它们的物理性质和电子密度分布。通过制造溶液处理的有机场效应晶体管（OFET）评估了它们作为半导体材料的潜力。DTB [32,34] Cz的角形异构体表现出最佳性能，空穴迁移率高达0.0044 cm 2 V -1 s -1在厚度约为ca的设备中。115 nm。特别是，基于DTB [32,34] Cz的设备的性能显示出对其有源层厚度的依赖性较小。
更新日期：2018-08-21
中文翻译：
七噻吩并蒽与内部咔唑的合成，区域选择性和有机场效应晶体管应用
并苯/杂并苯是研究最广泛的小分子有机半导体，始终具有线性结构。在这项工作中，三个稳定的，可溶的且呈角π扩展的七噻吩并并庚酮与内部咔唑，即噻吩并苯并稠合的咔唑（DTBCz）是通过四步串联方法合成的。从咔唑衍生物开始的串联合成导致有趣的异构体效应。合成区域选择性进行了详细讨论。通过紫外/可见吸收，光致发光，热重分析（TGA），差示扫描量热法（DSC），循环伏安法（CV）测量和理论计算研究了它们的物理性质和电子密度分布。通过制造溶液处理的有机场效应晶体管（OFET）评估了它们作为半导体材料的潜力。DTB [32,34] Cz的角形异构体表现出最佳性能，空穴迁移率高达0.0044 cm 2 V -1 s -1在厚度约为ca的设备中。115 nm。特别是，基于DTB [32,34] Cz的设备的性能显示出对其有源层厚度的依赖性较小。
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