吗啉基修饰的新型香豆素Fe~(3+)荧光探针化合物的合成及其性能

间苯二酚与乙酰乙酸乙酯经亲核取代反应制得7-羟基-4-甲基香豆素(1);1与碘甲烷在乙醚中反应制得7-甲氧基-4-甲基香豆素(2);2与N-溴代丁二酰亚胺在四氯化碳中经2步反应制得3-溴-4(溴甲基)-7-甲氧基香豆素(4);4在四氢呋喃溶剂中与吗啉反应合成了一种新型的基于香豆素的荧光探针化合物——3-溴-7-甲氧基-4-(吗啉代)-2H-吡喃-2-酮(5),其结构经~1H NMR,~(13)C NMR和MS表征。光学性能和金属离子识别性能研究结果表明:5的激发波长为340.15 nm,发射波长为408.35 nm;5对Fe~(3+)有良好的识别作用,在1.0×10-5mol·L~(-1)~9.0×10~(-5)mol·L~(-1)可定量检测Fe~(3+)含量。

Synthesis and Properties of A Novel Coumarin-based Fe3+ Fluorescent Probe Modified by Morpholin

7-Hydroxy-4-methyl coumarin(1) was prepared by nucleophilic substitution reaction of res-orcinol with ethyl acetoacetate. 7-Methoxy-4-methyl-coumarin(2) was synthesized by reaction of 1 with methyl iodide. 3-Bromo-4-(bromomethyl)-7-methoxy-coumarin(4) was prepared by two-step reaction of 2 with N-bromosuccinimide in CCl4 . A novel coumarin-based fluorescent probe, 3-bromo-7-me-thoxy-4-(morpholino)-2H-pyran-2-one(5), was synthesized by reaction of 4 with morpholine. The structure was characterized by 1 H NMR, 13 C NMR and MS. The optical properties of 5 were investiga-ted. The results showed theλex was 340. 15 nm andλem was 408. 35 nm. A study of the identification effect of 5 for different cations was carried out. The result showed that 5 exhibited good selectivity for Fe3+at 1. 0 × 10 -5 mol·L-1 ~9. 0 × 10 -5 mol·L-1 .