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Synthesis, crystal structure, photoluminescence, and electroluminescence properties of a new compound containing diphenylmethylene, carbazole, and malononitrile units

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Abstract

In this work, a new phenylethylene derivative, named 2-((3,5-di(9H-carbazol-9-yl)phenyl)(p-tolyl)methylene)malononitrile (DCPTMM), is synthesized and characterized by 1H NMR, 13C NMR spectroscopies, mass spectrum, and X-ray crystallography. Its photophysical properties are systematically studied and the result illustrates that DCPTMM shows aggregation-induced emission (AIE). The X-ray single crystal diffraction shows that the individual structure of crystals is monoclinic system with space group symbol P21/c and presents a twisted propeller-type structure as well as the packing structure of crystals has multiple types of hydrogen bonds (C–H⋯π and C–H⋯N) formed between adjacent molecules, and there is no π–π interaction between the aromatic rings, which is the main reason for the formation of AIE. Nondoped OLED fabricated with DCPTMM as light emitting layer emits greenish yellow light with a maximum emission peak of 554 nm and has relatively good performance with a maximum current efficiency of 5.53 cd/A and a maximum brightness of 6936 cd/m2.

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Acknowledgments

This work was supported by National Natural Science Foundation of China (No. 21875130) and Innovation and Entrepreneurship Training Program Project for College Students of University of Electronic Science and Technology of China (Nos. 201810614071 and 201810614770). The authors express their sincere thanks to the Advanced Computing Facilities of the Supercomputing Center of Computer Network Information Center of Chinese Academy of Sciences for all the theoretical calculations.

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Authors and Affiliations

  1. School of Information and Communication Engineering and School of Photoelectric Science and Engineering, University of Electronic Science and Technology of China, Chengdu, 611731, China

    Zhaofeng Shi, Dayong Zhang & Junsheng Yu

  2. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, China

    Jinnan Huo, Hongbo Wang & Heping Shi

  3. Department of Chemistry, Institute for Advanced Study, Division of Biomedical Engineering, Division of Life Science, State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials, The Hong Kong University of Science and Technology, Kowloon, Hong Kong, 999077, China

    Ben Zhong Tang

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  1. Zhaofeng Shi
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  2. Dayong Zhang
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  3. Jinnan Huo
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  4. Hongbo Wang
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  5. Junsheng Yu
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Correspondence to Junsheng Yu, Heping Shi or Ben Zhong Tang.

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Synthesis, crystal structure, photoluminescence and electroluminescence properties of a new compound containing diphenylmethylene, carbazole and malononitrile units (approximately 17.8 MB)

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Shi, Z., Zhang, D., Huo, J. et al. Synthesis, crystal structure, photoluminescence, and electroluminescence properties of a new compound containing diphenylmethylene, carbazole, and malononitrile units. Journal of Materials Research 34, 3000–3010 (2019). https://doi.org/10.1557/jmr.2019.173

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