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Anthracene-based derivatives: Synthesis, photophysical properties and electrochemical properties

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Abstract

A series of anthracene-based derivatives, namely, 9-(4-phenyl)anthracene(1), 9-(4-phenylethynyl)-anthracene(2) and 9, 10-bis(phenylethynyl)anthracene(3), was synthesized by the Suzuki/Sonogashira cross-coupling reactions in good yields. These compounds were fully characterized by X-ray crystallography, thermogravimetric analysis(TGA), differential scanning calorimetry(DSC), UV-Vis absorption and fluorescence(FL) spectroscopy, as well as density functional theory(DFT) calculations. Single-crystal X-ray analysis revealed that the packing structures were influenced by the terminal substitutions. All the compounds exhibited high thermal stability(T d=221—484 °C) and blue emission with a high quantum yield(Φ f =0.20—0.75). As the number of substituents increased, the decomposition temperatures(T d) of these compounds increased in the following order: 1<2<3. Experiments on the photophysical properties revealed that different substituents strongly affected the optical properties. In particular, compound 1b with the electron-withdrawing group(—CHO) exhibited a larger Stokes shift(113 nm) than the other compounds. Investigation of the electrochemical properties of these compounds showed that the HOMO-LUMO energy gaps(E gap) decreased obviously as the degree of conjugation increased.

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Authors and Affiliations

  1. College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. China

    Wan Zhang, Qi Wang & Xianfu Wei

  2. School of Printing and Packaging Engineering, Beijing Institute of Graphic Communication, Beijing, 102600, P. R. China

    Wan Zhang, Xing Feng, Li Yang, Youke Wu & Xianfu Wei

  3. RISE Bioeconomy, Research Institutes of Sweden, Stockholm, 11428, Sweden

    Li Yang

Authors
  1. Wan Zhang
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  2. Qi Wang
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  3. Xing Feng
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  4. Li Yang
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  5. Youke Wu
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  6. Xianfu Wei
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Corresponding author

Correspondence to Xianfu Wei.

Additional information

Supported by the National Natural Science Foundation of China(Nos.21602014, 61474144), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry of China, the Fund Program for the Scientific Activities of Selected Returned Overseas Professionals of Beijing, China, the Scientific Research Common Program of Beijing Municipal Commission of Education, China, the Doctoral Scientific Research Foundation of Beijing Institute of Graphic communication(BIGC)(No.KM201510015003) and the BIGC Project, China(Nos. 20190116002/043, 04190117001/019).

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Zhang, W., Wang, Q., Feng, X. et al. Anthracene-based derivatives: Synthesis, photophysical properties and electrochemical properties. Chem. Res. Chin. Univ. 33, 603–610 (2017). https://doi.org/10.1007/s40242-017-6431-4

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  • DOI: https://doi.org/10.1007/s40242-017-6431-4

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