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Synthesis and Performance of Imide-Based Small Molecules Containing Carbazole Groups with AIE Properties

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Abstract

Here, two novel naphthalimide derivatives SNI-Cz and SNI-DCz with AIE were designed and synthesized. The correctness of the two structures was characterized by NMR and HRMS. Their crystal structures, photophysical properties, electrochemical properties, thermal stabilities, fluorescence lifetime and yields have been characterized. Photoluminescence experiments revealed that SNI-DCz had superior properties due to the D-π-A-π-D structure and sliding away stacking of molecules. SNI-DCz exhibited weak fluorescence in pure DMF, with a significant AIE effect observed in the 40% water mixture and a sharp increase in fluorescence intensity was also observed. Cyclic voltammetry and thermogravimetric analysis indicated that SNI-DCz had good electron affinity and thermal stability. The excellent properties of SNI-DCz made it a promising emitter for optoelectronics.

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Acknowledgements

This work was supported by the Gansu Natural Science Foundation (20JR10RA219), the National Natural Science Foundation of China (Grand 51563014) and the Instrument Analysis Center of Lanzhou Jiaotong University.

Funding

This work was supported by the Gansu Natural Science Foundation (20JR10RA219, from Hui Zhang), the National Natural Science Foundation of China (Grand 51563014, from Tianzhi Yu) and the Instrument Analysis center of Lanzhou Jiaotong University.

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Authors and Affiliations

  1. Key Laboratory of Opto-Electronic Technology and Intelligent Control (Ministry of Education), Lanzhou Jiaotong University, Lanzhou, 730070, China

    Haina Wang, Hui Zhang & Tianzhi Yu

  2. Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd., Dong Yang, 322118, China

    Haina Wang

  3. School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou, 730070, China

    Yuling Zhao

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  1. Haina Wang
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  4. Yuling Zhao
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Contributions

Hui Zhang and Tianzhi Yu developed the idea of the study, participated in its design and coordination and helped to draft the manuscript. Haina Wang contributed to the acquisition and interpretation of data. Yuling Zhao did some testing works.All authors reviewed the manuscript.

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Correspondence to Tianzhi Yu.

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Wang, H., Zhang, H., Yu, T. et al. Synthesis and Performance of Imide-Based Small Molecules Containing Carbazole Groups with AIE Properties. J Fluoresc 33, 2503–2513 (2023). https://doi.org/10.1007/s10895-023-03249-5

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  • DOI: https://doi.org/10.1007/s10895-023-03249-5

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