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Halogenated Thienoacene Derivatives with Improved Emission Properties

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Chemical Research in Chinese Universities Aims and scope

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.

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Acknowledgements

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).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  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

    Jingmei Zhang, Zhihao Meng & Yonggang Zhen

  2. Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan, 430074, P. R. China

    Jingmei Zhang

  3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, P. R. China

    Zhihao Meng

  4. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong, 637000, P. R. China

    Ping He

  5. Key Laboratory of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University, Nanchang, 330022, P. R. China

    Panpan Yu

  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

    Wenping Hu

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  1. Jingmei Zhang
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  2. Zhihao Meng
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  3. Yonggang Zhen
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  4. Ping He
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Corresponding authors

Correspondence to Yonggang Zhen, Ping He, Panpan Yu or Wenping Hu.

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HU Wenping is an editorial board member for Chemical Research in Chinese Universities and was not involved in the editorial review or the decision to publish this article. The authors declare no conflicts of interest.

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Zhang, J., Meng, Z., Zhen, Y. et al. Halogenated Thienoacene Derivatives with Improved Emission Properties. Chem. Res. Chin. Univ. (2024). https://doi.org/10.1007/s40242-024-4038-0

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  • DOI: https://doi.org/10.1007/s40242-024-4038-0

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