Halogenated Thienoacene Derivatives with Improved Emission Properties

doi:10.1007/s40242-024-4038-0

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (4): 699-703.doi: 10.1007/s40242-024-4038-0

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Halogenated Thienoacene Derivatives with Improved Emission Properties

ZHANG Jingmei^1,2, MENG Zhihao^1,3, ZHEN Yonggang¹, HE Ping⁴, YU Panpan⁵, HU Wenping⁶

1. Advanced Innovation Center for Soft Matter Science and Engineering, State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, P. R. China;
2. Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074, P. R. China;
3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. China;
4. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637000, P. R. China;
5. Key Laboratory of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University, Nanchang 330022, P. R. China;
6. MOE Key Laboratory of Organic Integrated Circuits & Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Sciences, Tianjin University, Tianjin 300072, P. R. China

Received:2024-02-23 Online:2024-08-01 Published:2024-07-24
Contact: ZHEN Yonggang,zhenyg@buct.edu.cn;HE Ping,hp10004@cwnu.edu.cn;YU Panpan,ppyu@jxnu.edu.cn;HU Wenping,huwp@tju.edu.cn E-mail:zhenyg@buct.edu.cn;hp10004@cwnu.edu.cn;ppyu@jxnu.edu.cn;huwp@tju.edu.cn
Supported by:
This work was supported by the Fundamental Research Funds for the Central Universities, China (No. buctrc202103), the National Natural Science Foundation of China (Nos. 21975263, 22171019, 52373170), the Project of the China Petroleum and Chemical Corporation (No. 222131), the Open Project Programs of Wuhan National Laboratory for Optoelectronics, China (No. 2021WNLOKF005) and the Project of the State Key Laboratory of Fine Chemicals (Dalian University of Technology), China (No. KF2201).

Abstract

Abstract: Thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior mobility. However, there are scarce studies on the emission properties of thienoacenes to date. Herein, we synthesized fluorinated and chlorinated dibenzo[d,d′]thieno[3,2-b;4,5-b′]dithiophenes (DBTDTs) derivatives F6-DBTDT and Cl6-DBTDT by sulfoxide cyclization, significantly lowering the energy levels relative to the parent compound DBTDT. According to single crystal structure analysis, F6-DBTDT molecules adopt one-dimensional slipped stacking with close π-π interactions of 3.43 Å (1 Å=0.1 nm), which is different from the parent compound DBTDT with herringbone stacking motif. Interestingly, the halogenated DBTDT derivatives exhibit enhanced emission properties both in solution and in the solid state, opening up possiblities to improve photoluminescence of thienoacences by halogenation.

Key words: Thienoacene, Halogenation, Photoluminescence, Aggregation structure

ZHANG Jingmei, MENG Zhihao, ZHEN Yonggang, HE Ping, YU Panpan, HU Wenping. Halogenated Thienoacene Derivatives with Improved Emission Properties[J]. Chemical Research in Chinese Universities, 2024, 40(4): 699-703.

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Halogenated Thienoacene Derivatives with Improved Emission Properties

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