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Chemical Research in Chinese Universities

, Volume 33, Issue 4, pp 603–610 | Cite as

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

  • Wan Zhang
  • Qi Wang
  • Xing Feng
  • Li Yang
  • Youke Wu
  • Xianfu WeiEmail author
Article

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.

Keywords

Anthracene-based derivative Photophysical property Structure-property relationship Blue-emitting material 

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Supplementary material

40242_2017_6431_MOESM1_ESM.pdf (1.8 mb)
Anthracene-based Derivatives, Synthesis, Photophysical Properties and Electrochemistry

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH 2017

Authors and Affiliations

  • Wan Zhang
    • 1
    • 2
  • Qi Wang
    • 1
  • Xing Feng
    • 2
  • Li Yang
    • 2
    • 3
  • Youke Wu
    • 2
  • Xianfu Wei
    • 1
    • 2
    Email author
  1. 1.College of Light Industry Science and EngineeringNanjing Forestry UniversityNanjingP. R. China
  2. 2.School of Printing and Packaging EngineeringBeijing Institute of Graphic CommunicationBeijingP. R. China
  3. 3.RISE BioeconomyResearch Institutes of SwedenStockholmSweden

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