本科生综合实验:4-[二(4-甲基苯)氨基]苯甲醛合成与变色性能研究

Comprehensive undergraduate experiment:synthesis and chromism of 4-[bis(4-methylphenyl)amino]benzaldehyde

针对有机合成实验缺少性质研究、仪器分析实验分析方法相对独立的问题,本项目基于机械致荧光变色材料在化学前沿领域的研究,设计了一个本科生综合实验。以4,4′-二甲基三苯胺为原料,通过Vilsmeier-Haack反应合成了4-[二(4-甲基苯)氨基]苯甲醛,并通过质谱、红外吸收光谱和核磁共振波谱对其结构进行了表征;然后通过紫外-可见吸收光谱、荧光光谱等对其溶剂化变色和机械致荧光变色现象进行了研究,并通过X射线粉末衍射对其机械致荧光变色机理进行了探讨。本项目将有机合成与仪器分析实验相结合,形成合成及变色性能一体化研究,实验综合性强,现象有趣,是一个兼具趣味性、科学性和综合性的本科生创新实验。该实验可以很好地激发学生对化学研究的兴趣,锻炼多项实验操作能力,提升学生的综合科研素质。

To solve the problems of the lack of property research in organic synthesis experiments and the relative independence of instrumental analytical methods in experiments,we designed a comprehensive undergraduate experiment based on mechanofluorochromic materials.In this project,4-[bis(4-methylphenyl)amino]benzaldehyde was synthesized via the Vilsmeier-Haack reaction using 4,4′-dimethyltriphenylamine as the raw material.The product was then characterized by mass spectrometry,infrared absorption spectroscopy,and nuclear magnetic resonance spectroscopy.The solvatofluorochromism and mechanofluorochromism of the target material were studied using ultraviolet-visible absorption spectroscopy,fluorescence spectroscopy,etc.Furthermore,the mechanism of mechanofluorochromism was determined using powder X-ray diffraction.Organic synthesis and a series of instrumental analytical methods were combined to form an integrated experiment.The experiment is interesting,scientific,and comprehensive for undergraduates as a creative exercise;moreover,it can inspire their interest in chemical research,cultivate a variety of experimental operation abilities,improve creative-thinking skills,and encourage the development of effective solutions to existing problems in chemical experiments.