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Synthesis, self-assembly and photophysical properties of AIEE-active triphenylamine-based discotic liquid crystals

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Abstract

A series of triphenylamine-based discotic liquid crystals (DLCs) containing three α-cyanostilbene units and a central triphenylamine were designed and prepared using Suzuki coupling and Knoevenagel reaction. Polarized optical microscopy, differential scanning calorimetry and X-ray diffraction were employed to investigate the textures, phase transition temperatures and self-assembly structures, demonstrating that all the compounds exhibit Colsqu/p4mm phase. The only Colsqu/p4mm phase could be observed with elongation of terminal alkyl chains, which might be attributed to the central propeller-shaped triphenylamine unit and α-cyanostilbene units with different configurations. These DLCs displayed temperature-dependent emission behavior and high fluorescence intensity even in isotropic state. Interestingly, these DLCs are insensitive for 365 nm UV light in bulk state, whereas sensitive in solution state. Distinct positive solvatochromism in different organic solvents and aggregation-induced enhanced emission (AIEE) behavior in tetrahydrofuran-H2O mixtures could be observed due to the intramolecular charge transfer (ICT) and twisted configuration induced by triphenylamine and α-cyanostilbene units, respectively. The optimized geometry and spatial distribution of the HOMO and LUMO obtained from density functional theory calculations well demonstrated ICT and twisted conformation. Therefore, this work will provide a rational molecular design strategy to construct AIEE-active liquid crystals with excellent properties and wide potential applications.

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Acknowledgements

This work was supported by China West Normal University Doctor Startup Fund (No: 412821), Major project fund of Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province (No: CSPC202101) and Scientific Research Fund Project of Yunnan Provincial Department of Education (No. 2021J0011). We thank beamline 1W2A at Beijing Synchrotron Radiation Facility (BSRF), China.

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  1. Chemical Synthesis and Pollution Control, Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan, 637002, People’s Republic of China

    Xiaotong Liu, Nana Li, Yida Pang & Yulong Xiao

  2. School of Forensic Medicine, Kunming Medical University, Kunming, Yunnan, 650500, People’s Republic of China

    Shuhua Li

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  1. Xiaotong Liu
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Liu, X., Li, N., Pang, Y. et al. Synthesis, self-assembly and photophysical properties of AIEE-active triphenylamine-based discotic liquid crystals. J IRAN CHEM SOC 19, 4411–4421 (2022). https://doi.org/10.1007/s13738-022-02611-x

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