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Aggregation‐induced Emission Properties of Triphenylamine Chalcone Compounds

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Abstract

Two triphenylamine chalcone derivatives 1 and 2 were synthesized through the Vilsmeier-Haack reaction and Claisen-Schmidt condensation reaction. Through ultraviolet absorption spectroscopy and fluorescence emission spectroscopy experiments, it was confirmed that these two compounds exhibited good aggregation-induced emission (AIE) behavior in ethanol/water mixtures. The solvent effect test showed with the increase of the orientation polarizability of the solvent, the Stokes shift in the solvent of compound 1 and compound 2 shows a linear change trend. Through solid state fluorescence test and universal density function theory (DFT), the existence of π-π stacking interaction in the solid state of the compound has been studied, resulting in weak fluorescence emission. pH has no effect on the fluorescence intensity of the aggregate state of excited state intramolecular proton transfer (ESIPT) molecules in an acidic environment, but greatly weakens its fluorescence intensity in an alkaline environment. Cyclic voltammetry (CV) test shows that compound 1 was more prone to oxidation reaction than compound 2. The results of thermal stability test show that the thermal stability of compound 1 was better than that of compound 2, indicating that triphenylamine chalcone derivatives can improve the thermal stability of compounds by increasing the number of branches.

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Data Availability

The 1 H NMR, 13 C NMR HR-ESI-Ms of the 1 and 2 are detailed in the Supporting information. These materials are available free of charge via the Internet.

Code Availability

Not applicable.

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Authors and Affiliations

  1. School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou, 730050, China

    Ying-Peng Zhang, Qi Teng, Yun-Shang Yang & Jing-Qi Cao

  2. State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, 730000, Lanzhou, China

    Ji-Jun Xue

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  1. Ying-Peng Zhang
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Contributions

Ying-Peng Zhang, contributed to the conception of the study;

Qi Teng, performed the experiment and wrote the manuscript;

Yun-Shang Yang, contributed significantly to analysis and manuscript preparation;

Jing-Qi Cao, performed the data analyses;

Ji-Jun Xue, helped perform the analysis with constructive discussions.

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Correspondence to Yun-Shang Yang.

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Zhang, YP., Teng, Q., Yang, YS. et al. Aggregation‐induced Emission Properties of Triphenylamine Chalcone Compounds. J Fluoresc 31, 807–815 (2021). https://doi.org/10.1007/s10895-021-02711-6

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  • DOI: https://doi.org/10.1007/s10895-021-02711-6

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