香豆素修饰的均三嗪环荧光探针的合成及其光学性能

Synthesis and Optical Properties of Triazine Ring Modified by Coumarin

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3-溴-1-丙醇经取代反应制得3-（4,6-二氯-1,3,5-三嗪-2-氧基）-1-丙醇（4）;1和4分别与三聚氯氰经取代反应合成了两种新型的单侧臂探针化合物——7-（4,6-二氯-1,3,5-三嗪-2-氧基）-4-甲基香豆素（3）和7-[3-（4,6-二氯-1,3,5-三嗪-2-氧基）丙氧基]-4-甲基香豆素（5）,其结构经1H NMR,13C NMR和HR-ESI-MS表征。光学性能研究结果表明,在324.29 nm波长激发下,5的发射波长位于371.80 nm。5在甲醇中对Cu2＋具有良好的识别作用,在浓度1.0×10^-6mol·L^-1~5.0×10^-5mol·L^-1能定量检测Cu^2＋含量。

7-Hydroxy-4-methyl-coumarin （1） was prepared by nucleophilic substitution reaction of resorcinol with ethyl acetoacetate. 7- （3-Hydroxypropoxy） -4-methyl-2H-chromen-2-one （4） was pre- pared by substitution reaction of I with 3-bromo-l-propanol. Two novel triazine derivatives as fluores- cent probes modified by coumarin, 7-hydroxy-4-methyl-coumarin （3） and 7- { 3- [ （4,6-dichloro-1,3, 5-triazin-2-yl ） oxy ] propoxy } -4-methyl-2H-chromen-2-one （ 5 ）, were synthesized by substitution reac- tion of 1 or 4 with cyanuric chloride, respectively. The structures were characterized by l H NMR, 13C NMR and HR-ESI-MS. The optical properties were investigated. The results showed that λmax of 5 was 371.80 nm. 5 exhibited good selectivity for Cu^2＋ at 1.0 ×10^-6mol·L^-1~5.0×10^-5mol·L^-1.