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以4-卤代间苯二酚为原料经甲酰化反应合成了2,4-二羟基-5-卤代苯甲醛,再通过Knoevenagel缩合反应合成了5种香豆素衍生物,最后经Mannich反应获得了5种未见文献报道的香豆素类荧光功能化合物.所得的荧光化合物的结构均用1H NMR,IR,MS和元素分析等方法进行了表征,并且对该类化合物的荧光性质及对金属离子的响应进行了研究.结果发现,由于光诱导电子转移(PET)的作用,在Mannich反应后,目标产物的荧光强度弱于反应前,而当该产物与金属离子配合后,PET作用减弱,荧光强度得到恢复.
2,4-Dihydroxy-5-halogenobenzaldehyde was synthesized from 4-haloresorcinol by formylation reaction. Five coumarin derivatives were synthesized by Knoevenagel condensation reaction. Finally, Mannich Five novel coumarin fluorescent functional compounds were obtained, and the structures of the obtained fluorescent compounds were characterized by 1H NMR, IR, MS and elemental analysis, and the fluorescence properties of these compounds were also studied The results showed that the fluorescence intensity of the target product was weaker than that before the reaction due to the photoinduced electron transfer (PET), and after the Mannich reaction, the interaction of PET with the metal ion Weakened, the fluorescence intensity was restored.