大学化学 >> 2019, Vol. 34 >> Issue (1): 48-53.doi: 10.3866/PKU.DXHX201805007

化学实验 上一篇    下一篇

四苯乙烯的合成、表征及在爆炸物检测中的应用——介绍一个大学化学综合实验

何田,顾峥烨,尹守春*()   

  • 收稿日期:2018-05-03 发布日期:2019-01-16
  • 通讯作者: 尹守春 E-mail:yinsc@hznu.edu.cn
  • 基金资助:
    浙江省"十二五"省级实验教学示范中心重点建设项目(浙教办函（2015）173号);浙江省MOOC/SPOC课程培育项目;杭州师范大学高等教育课堂教学改革研究项目

Synthesis and Characterization of Tetraphenylethylene and Its Application for Explosive Detection: An Introduction of a Comprehensive Chemical Experiment

Tian HE,Zhengye GU,Shouchun YIN*()   

  • Received:2018-05-03 Published:2019-01-16
  • Contact: Shouchun YIN E-mail:yinsc@hznu.edu.cn
  • Supported by:
    浙江省"十二五"省级实验教学示范中心重点建设项目(浙教办函（2015）173号);浙江省MOOC/SPOC课程培育项目;杭州师范大学高等教育课堂教学改革研究项目

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摘要：

因具有聚集诱导发光特性、螺旋桨结构的四苯乙烯及其衍生物，在有机光电材料、荧光传感和生物成像等领域表现出优异的荧光性能。本实验以二苯甲酮为原料，利用McMurry偶联反应合成四苯乙烯。采用萃取、干燥和柱层析等手段对产物进行分离和纯化，通过熔点测定、核磁共振氢谱、核磁共振碳谱和质谱对其结构进行表征后，使用苦味酸作为模型化合物，利用荧光光谱测定其对爆炸物的荧光检测极限。本实验寓科研热点于实验教学中，不仅提高了学生的实验操作技能，而且有助于学生了解具有聚集诱导发光性能的四苯乙烯及其衍生物的研究现状和应用前景，激发了学生的科研兴趣和创新意识。

关键词: 四苯乙烯, 聚集诱导发光, 综合实验, 荧光, 爆炸物检测

Abstract:

Tetraphenylethylene and its derivatives with propeller structure have excellent fluorescence properties, which can be applied to the fields of organic photo-electric materials, fluorescence sensing and biological imaging due to the aggregation-induced fluorescence property. In this experiment, tetraphenylethylene was synthesized by McMurry coupling reaction using benzophenone as starting materials. The target compound was separated and purified by extraction, drying and column chromatography, and its structure was characterized by the melting point measurement, 1H NMR, 13C NMR, and MS. The fluorescence detection limit for explosives was determined by fluorescence spectra using picric acid as a model compound. This experiment with the research focuses can improve the students' experimental skills, help students to understand the current status and applications of tetraphenylethylene and its derivatives with aggregation-induced fluorescence property, and stimulate students' interest in scientific research and innovation consciousness.

Key words: Tetraphenylethylene, Aggregation-induced emission, Comprehensive experiment, Fluorescence, Explosive detection