4'-(1,2,4-三氮唑苯基)-4,2':6',4''-三联吡啶的合成、表征与发光性质——推荐一个有机化学综合创新性实验

Synthesis,Characterizaiton and Fluorescence Property of 4′-(1,2,4-Triazolylphenyl)-4,2′:6′,4′′-Terpyridine:A proposed comprehensive and innovative organic chemistry experiment

以1,2,4-三氮唑、对氟苯甲醛为原料,通过亲核取代反应制备4′-(1,2,4-三氮唑基)苯甲醛,然后与4-乙酰基吡啶在氢氧化钾提供的碱性环境作用下反应,并最终以氨水为氮源合成了4′-(1,2,4-三氮唑基苯基)-4,2′:6′,4′′-三联吡啶(L)。通过对比溶剂、反应时间,反应物用量等因素确定了产率最高的反应条件。运用熔点、红外光谱、核磁共振氢谱、碳谱、X-射线单晶衍射对该三联吡啶衍生物的结构进行了表征,并进行了固体紫外可见光谱与荧光光谱测试,进一步确认了其结构与性质之间的关系。旨在提高本科学生的有机实验操作能力和对有机化学实验原理的进一步理解,从而更好地提升学生的科研兴趣与创新能力。

In this experiment,1,2,4-triazole and p-fluorobenzaldehyde were used as raw materials to prepare 4′-(1,2,4-triazolyl)-benzaldehyde by a nucleophilic substitution reaction.The title compound was obtained with 4′-(1,2,4-triazo-lyl)-benzaldehyde and 4-acetylpyridine as raw materials in an alkaline environment provided by potassium hydroxidetheas well as the presence of aqueous ammonium worked as nitrogen source.The reaction conditions with the highest yieldwere determined by comparing factors such as solvent,reaction time,and amount of reactants.The structure of the titlecompound was characterized by melting point,IR,~1H and13C NMR,and x-ray single crystal diffraction.In addtion,UV-vis and fluorescence spectrum of solid-state samples were obtained,which further confirming the relationship betweenstructures and properties.It was proposed as an organic chemistry experiment as it would improve the undergraduate stu-dents′ experimental operation ability and understanding of experimental principles of organic chemistry and it would betterenhance students′ scientific research interest and innovation ability.