University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2110095.doi: 10.3866/PKU.DXHX202110095

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Ultrasonic-Assisted Synthesis of Tetraphenylethylene and Its Derivatives, and the Characterization of Their Photo- and Electro- Properties

Nana Sun, Fujie Xu, Haozhe Jin, Huanyu Ren, Langui Xie(), Zhi Su()   

  • Received:2021-10-29 Accepted:2021-11-04 Published:2022-04-08
  • Contact: Langui Xie,Zhi Su E-mail:xielg@njnu.edu.cn;zhisu@njnu.edu.cn

Abstract:

The typical aggregation-induced emission (AIE) property of tetraphenylethylene and its derivatives has been widely reported, leading to broad applications in OLED, fluorescent probes, and biochemical imaging. Due to advanced achievements, an AIE-related comprehensive experiment for undergraduates would encourage them to pursue scientific studies. In the original experiment, tetraphenylethylene (TPE) was synthesized using the McMurry coupling reaction, which takes 8 h to complete. In our modified experiment, using ultrasonic assistance, the synthesis was shortened to 2 h. We have added two parallel control complexes, methoxyl-(TPE-OMe) and bromide-derivatives (TPE-Br), with the push or pull electro effects, to observe UV-Vis absorption, fluorescence emission, and redox potential. The student can understand the chemical principle of red- and blue-shifts of maximum emissions by directly observing them with TPE and its derivative. Compared to the original experiment, our modified experiment made significant improvements, such as introducing parallel experiments to promote scientific thought and ultrasonic-assisted synthesis to shorten the synthesis, making the experiment more innovative, environmental-friendly, and efficient.

Key words: Aggregation-induced emission (AIE), Tetraphenylethylene derivatives, Ultrasonic-assisted synthesis, Cyclic voltammetry