分析化学2025，Vol.53Issue(7)：1108-1117,10.DOI:10.19756/j.issn.0253-3820.251054
吲哚-3-甲酰肼修饰的芘席夫碱化合物作为铜离子荧光探针的合成与应用
Synthesis and Applications of Indole-3-formylhydrazine Modified Pyrene Schiff Base Compound as Copper Ion Fluorescence Probe
摘要
Abstract
In this work,a fluorescent probe PIN was synthesized using indole-3-carbohydrazide and pyrenecarboxaldehyde as raw materials.PIN showed weak fluorescence emission in aqueous solution with acetonitrile volume fraction of 70％.However,when Cu2+was added to this aqueous solution of PIN,a new fluorescence emission peak appeared at 495 nm,and the intensity of this peak gradually increased with the increase of concentration of Cu2+,and also caused a significant change in the fluorescence color of the solution.In contrast,the addition of 15 kinds of other common metal ions did not cause such change.The detection limit of PIN for Cu2+was 78.7 nmol/L,which was much lower than the maximum permitting level of Cu2+in drinking water in hygienic standard for drinking water in China.Therefore,PIN was a highly selective and sensitive fluorescence-enhanced probe for Cu2+.Meanwhile,the addition of Cu2+could also cause a new absorption peak at 440 nm in the ultraviolet-visible absorption spectrum of the aqueous solution of PIN,and meanwhile the colorless PIN solution changed into yellow,exhibiting the performance of PIN as a colorimetric probe for Cu2+.By fitting with the Levenberg-Marquardt algorithm equation,the binding ratio of PIN to Cu2+was 2:1,and the binding constant was 3.42×1012 L2/mol2.In addition,the binding mode of PIN with Cu2+was explored by using proton nuclear magnetic resonance(1H NMR)titration experiments and density functional theory simulations.The results showed that the addition of Cu2+could cause the aggregation of PIN molecules to form excimers,thus showing highly selective recognition.Finally,PIN was made into a simple test strip,which could achieve rapid and convenient fluorescence detection of Cu2+in actual water samples.关键词
铜离子(Ⅱ)/荧光探针/吲哚-3-甲酰肼/芘/席夫碱Key words
Copper ion(Ⅱ)/Fluorescence probe/Indole-3-carbohydrazide/Pyrene/Schiff base引用本文复制引用
王沐溪,黄振煜,林晓峰,雷晓兰,孙健,马立军..吲哚-3-甲酰肼修饰的芘席夫碱化合物作为铜离子荧光探针的合成与应用[J].分析化学,2025,53(7):1108-1117,10.基金项目
国家自然科学基金项目(Nos.22273027,22373024)资助. Supported by the National Natural Science Foundation of China(Nos.22273027,22373024). （Nos.22273027,22373024）
