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

Wan Zhang; Qi Wang; Xing Feng; Li Yang; Youke Wu; Xianfu Wei

doi:10.1007/s40242-017-6431-4

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (4) : 603 -610. DOI: 10.1007/s40242-017-6431-4

Article

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

Wan Zhang ¹^,²
, Qi Wang ¹
, Xing Feng ²
, Li Yang ²^,³
, Youke Wu ²
, Xianfu Wei ¹^,²^,^f

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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.

Keywords

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

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Wan Zhang, Qi Wang, Xing Feng, Li Yang, Youke Wu, Xianfu Wei. Anthracene-based derivatives: Synthesis, photophysical properties and electrochemical properties. Chemical Research in Chinese Universities, 2017, 33(4): 603-610 DOI:10.1007/s40242-017-6431-4

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