大学化学 >> 2022, Vol. 37 >> Issue (5): 2110095.doi: 10.3866/PKU.DXHX202110095

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四苯乙烯及其衍生物超声辅助合成与光电性能研究

孙娜娜, 许傅杰, 金浩哲, 任焕宇, 谢兰贵(), 苏志()   

  • 收稿日期:2021-10-29 录用日期:2021-11-04 发布日期:2022-04-08
  • 通讯作者: 谢兰贵,苏志 E-mail:xielg@njnu.edu.cn;zhisu@njnu.edu.cn
  • 作者简介:Email: xielg@njnu.edu.cn (谢兰贵)
    Email: zhisu@njnu.edu.cn (苏志)
  • 基金资助:
    江苏省特聘教授基金

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

摘要:

四苯乙烯及其衍生物被广泛报道具有典型的聚集诱导发光(AIE)性能,在有机发光二极管、荧光离子探针、生物化学成像等诸多领域有着广阔的应用前景。以此为背景,可以将相关前沿议题转化为本科综合实验教学方案。本文针对现有的实验教学方案设计进行了探究和改进,在原有使用McMurry偶联反应制备四苯乙烯的实验方案基础上,利用生色团上不同取代基的推拉电子效应设计平行对照试验,合成溴代、甲氧基取代的四苯乙烯衍生物,实现了荧光发射光谱最大峰波长的显著移动,使得在紫外灯下即可观察到荧光从蓝色到黄绿色的变化。利用超声辅助合成的方法,成功将反应时间从原有的6–8 h压缩至2 h,使之更适应本科教学实验所需的时间空间。除光学性能表征外,本实验还综合了循环伏安法表征产物的能带结构。本实验针对原有方案进行了诸多改进,引入平行实验锻炼科学思维、别出心裁地引入超声辅助合成法,极大地缩短了反应时间,展现出较强的前沿性、绿色性和高效性。

关键词: 聚集诱导发光(AIE), 四苯乙烯衍生物, 超声辅助合成, 循环伏安法

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

MSC2000: 

  • G64