title: Antiaromatic characteristic analysis of 1,4-diazapentalene derivatives: a theoretical study.
abstract: 1,4-Diazapentalene heteroacenes are potential n-type semiconductors that could be used as a new type of material for organic field-effect transistors (OFETs), but their synthesis is still challenging due to their antiaromaticity. The study on their structure-stability relationship should provide useful guidance to the design of stable diazapentalenes. We examined the stability of several types of heteroacenes bearing the 1,4-diazapentalene core using NICS(1)zz calculations. The influence of the fusion pattern, the introduction of substituents, and the incorporation of other heterocycles on the antiaromaticity of the central 1,4-diazapentalene core was systematically studied. It was found that the linear fusion of aromatic rings to the antiaromatic core increases the stability of the heteroacene. The fusion of electron-poor heterocyclic rings also enhances the stability effectively, whereas the fusion of electron-rich heterocyclic rings destabilizes the system. In addition, the combination of the linear fusion pattern or introduction of electron-poor heterocyclic rings to the antiaromatic core reduces the reorganization energy for electron transport, suggesting a way to achieve better n-type semiconductors.
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.|‡University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
authors: Jie
authors: J
authors: Zheng
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.|‡University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
authors: Xuhui
authors: X
authors: Zhuang
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.|‡University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
authors: Li
authors: L
authors: Qiu
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.|‡University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
authors: Yu
authors: Y
authors: Xie
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.
authors: Xiaobo
authors: X
authors: Wan
authors: †Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101 Shandong, People's Republic of China.
authors: Zhenggang
authors: Z
authors: Lan
mesh_terms: D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory; D012666:Semiconductors; D014173:Transistors, Electronic
chemical_list: C000599599:1,4-diazapentalene; D006576:Heterocyclic Compounds, 4 or More Rings