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Crystallographic and Computational Investigations of Triphenylamine/Anthraquinone Hybrids

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Abstract

Understanding of relationship between structure and property of thermally activated delayed fluorescence (TADF) materials is essential for developing efficient TADF materials. To investigate the substituent effect of electron donors on luminescent properties of TADF materials, a series of single crystals based on triphenylamine (TPA)/anthraquinone (AQ) hybrids namely 1-TPA-AQ, 2-TPA-AQ, 1,8-2TPA-AQ, 2,6-2TPA-AQ have been prepared in this work. Interestingly, it is demonstrated that the substituent site of TPA unit has an important impact on the conformation of AQ for the first time. The planarity of the AQ units in these four molecules is in the order 2,6-2TPA-AQ > 2-TPA-AQ ≈ 1-TPA-AQ > 1,8-2TPA-AQ, which is associated with the molecule symmetry. In addition, intermolecular interactions in these crystals are also investigated. In α-substituted AQ derivatives (1-TPA-AQ and 1,8-2TPA-AQ) typical π–π intermolecular interactions may account for their normal TADF but weak emission in solid state. In contrast, β-substituted AQ derivatives (2-TPA-AQ and 2,6-2TPA-AQ) display weak intermolecular interactions, which are beneficial to restricting molecular motions and to suppressing the non-radiative decay, resulting in efficient TADF and aggregation-induced emission properties simultaneously.

Graphic Abstract

It is demonstrated that the substituent site of triphenylamine unit on anthraquinone (AQ) group has an important impact on the conformation of AQ.

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Acknowledgements

This work was supported Qing Lan Project of Jiangsu Province, the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 19KJB150006) and China Postdoctoral Science Foundation Funded Project (No. 2020M681464).

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Authors and Affiliations

  1. College of Life Sciences and Chemistry, Jiangsu Key Laboratory of Biofunctional Molecule, Jiangsu Second Normal University, Nanjing, 211222, China

    Bin Huang

  2. State Key Laboratory of Bioelectronics, Jiangsu Key Laboratory for Biomaterials and Devices, School of Biological Sciences and Medical Engineering, Southeast University, Nanjing, 210096, China

    Bin Huang

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Correspondence to Bin Huang.

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Huang, B. Crystallographic and Computational Investigations of Triphenylamine/Anthraquinone Hybrids. J Chem Crystallogr 52, 53–61 (2022). https://doi.org/10.1007/s10870-021-00890-5

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