Yang Fan, Wang Cui, Liang Laiyu, Wang Zhiqiang, You Xiaoxiao, Shao Guangwei, Wu Di, Xia Jianlong
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, No. 122 Luoshi Road, 430070, Wuhan, China.
Wuhan 2nd Ship Design & Research Institute, No. 19 Yangqiaohu road, 430205, Wuhan, China.
Chemistry. 2024 Jul 2;30(37):e202401074. doi: 10.1002/chem.202401074. Epub 2024 Jun 14.
The backwardness of n-type organic semiconductors still exists compared with the p-type counterparts. Thus, the development of high-performance n-type organic semiconductors is of great importance for organic electronic devices and their integrated circuits. In recent years, azabenzannulated perylene diimide (PDI), as one of immense bay-region-annulated PDI derivatives, has drawn considerable attentions. However, the electronic mobilities of azabenzannulated PDI derivatives are barely satisfactory. In this contribution, the peripheral benzene ring in azabenzannulated PDI 2 was fused to the ortho position by intramolecular C-H arylation cyclization. This endows the resultant azabenzannulated PDI 4 a planar configuration as well as electron deficient pentagonal ring. As a result, the electronic mobility of 4 is almost two orders of magnitude higher than that of the nonfused azabenzannulated PDI 2. This work shall pave a new avenue in elevating the performance of azabenzannulated PDI in organic electronics.
与p型有机半导体相比，n型有机半导体仍然较为落后。因此，高性能n型有机半导体的开发对于有机电子器件及其集成电路至关重要。近年来，氮杂苯并苝二酰亚胺（PDI）作为具有巨大湾区稠合的PDI衍生物之一，受到了广泛关注。然而，氮杂苯并苝二酰亚胺衍生物的电子迁移率仍不尽人意。在本研究中，通过分子内C-H芳基化环化反应，将氮杂苯并苝二酰亚胺2中的外围苯环稠合到邻位。这使得所得的氮杂苯并苝二酰亚胺4具有平面构型以及缺电子的五元环。结果，4的电子迁移率比未稠合的氮杂苯并苝二酰亚胺2高出近两个数量级。这项工作将为提高氮杂苯并苝二酰亚胺在有机电子学中的性能开辟一条新途径。
