基于氢键策略卟啉荧光探针的合成及其在2,4,6-三硝基苯酚选择性检测中的应用

The synthesis of porphyrin fluorescent probe based on hydrogen bond strategy and the application on selective detection of 2,4,6-Trinitrophenol

考虑到苦味酸带来严重的社会安全和环境危害问题,发展快速、选择性痕量检测硝基芳烃爆炸物苦味酸的方法极为重要。本文结合密度泛函理论计算,设计合成带有脲基团的锌卟啉荧光探针分子用于含硝基芳烃的荧光检测;荧光测试结果证实带有脲基团的锌卟啉ZH-1能够快速、选择性检测苦味酸,荧光淬灭明显,其它一硝基芳烃、二硝基芳烃不能淬灭锌卟啉ZH-1荧光;锌卟啉ZH-1和苦味酸的核磁共振氢谱滴定实验证实脲基团与硝基之间存在明显的氢键作用,从而导致快速荧光响应。上述研究结果表明:氢键策略可应用于荧光探针分子设计用于苦味酸快速和选择性检测。锌卟啉ZH-1荧光探针结构经1H NMR、13C NMR和高分辨质谱表征。

In consideration of social safety and environmental risk of picric acid, fast and selectively detection of nitro-aromatic explosives PA is vital important. In this paper,combining with the density functional theory calculations,we design and synthesize the zinc porphyrin fluorescence probes bearing urea functional groups for the fluorescence detection of nitroaromatics. The results show that the zinc porphyrin ZH-1 bearing urea functional groups can fast and selectively detect picric acid with significantly fluorescence quenching. And other mononitroaromatics,dinitroaromatics can not quench the zinc porphyrin ZH-1 fluorescence. 1H NMR titration of Zinc porphyrin ZH-1 upon the addition of PA have confirmed the obvious hydrogen bonding generated between the urea functional group and the nitro group,resulting in a rapid fluorescence response. It was demonstrated that the hydrogen bonding strategy can be applied to design fluorescent probe molecules for rapid and selective detection of picric acid. The structure of the zinc porphyrin ZH-1 fluorescent