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.
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。
Keywords: comprehensive experiment; mechanoflurochromism; solvatofluorochromism; triphenylamine compounds.