新型咪唑[4,5-f][1,10]邻菲啰啉衍生物的合成及对Zn^(2+)荧光识别

Synthesis of four kinds of novel imidazo [4,5-f][1,10] phenanthroline derivatives and fluorescent identification of Zn^(2+)

邻菲啰啉二酮(1)在醋酸与醋酸铵的作用下与芳香醛通过脱水缩合构筑咪唑环,首次合成了3个新型芳基咪唑化合物(3a^3c).利用IR和1 H NMR等对目标分子3进行了结构表征.首次探究了11种金属离子对目标产物3的荧光猝灭,选取了包括主族和副族的11种金属离子Ca^(2+)、Cr^(3+)、Hg^(2+)、Al^(3+)、Mn^(2+)、Na+、Pb^(2+)、Fe^(3+)、Cu^(2+)、Zn^(2+)、Fe^(2+).通过荧光测试研究了金属离子的荧光猝灭现象,并通过经典的方法计算出了荧光猝灭系数KSV.研究结果表明:Zn^(2+)对配体3a、3b、3c均产生优良的猝灭效果,并产生红移,因此可对Zn^(2+)进行荧光识别.荧光猝灭系数KSV的计算结果表明,金属离子的最低检出限可达10^(-5)mol/L.利用产生荧光猝灭现象可以广泛应用于金属离子荧光探针识别,从而达到检测金属离子的目的.因此,目标产物可作为Zn^(2+)的荧光探针.

Three novel aryl imidazole compounds （3a-3c） were first synthesized by reaction 1,10- phenanthroline-5,6-dione （1） with aromatic aldehydes in the presence of acetic acid and ammonium acetate. The structures of target molecules were characterized by IR and 1 H NMR. This paper select- ed including main group and subgroup, 11 kinds of metal ions Ca2＋ ,Cr3＋ ,Hg2＋ ,AP＋ ,Mn2＋ ,Na＋ , Pb2＋ ,Fe3＋ ,Cu2＋ ,Zn2＋ ,Fe2＋. The fluorescence quenching of 11 kinds of metal ions on four target compounds was also screened. By fluorescence test the impact on the target molecule fluorescence in- tensity-fluorescence quenching was studied, and quenching coefficient Ksv, was calculated according to the Stern-Volmer equation. It was found that, Zn2＋ exhibited excellent quenching effect on 3a,3b and 3c,and produced red shift which had important value. The results of Ksv showed that the lowest of detection of metal ions is 10 μmol/L. This phenomenon can be widely used in metal ion sensing, and achieve the function of detecting metal ions effectively. Therefore, the target product can he used as a fluorescent probe Zn2＋.