Synthesis and Applications of Indole-3-formylhydrazine Modified Pyrene Schiff Base Compound as Copper Ion Fluorescence Probe
10.19756/j.issn.0253-3820.251054
- VernacularTitle: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
- Author:
Mu-Xi WANG
1
;
Zhen-Yu HUANG
;
Xiao-Feng LIN
;
Xiao-Lan LEI
;
Jian SUN
;
Li-Jun MA
Author Information
1. 华南师范大学化学学院,广州 510006
- Keywords:
Copper ion(Ⅱ);
Fluorescence probe;
Indole-3-carbohydrazide;
Pyrene;
Schiff base
- From:
Chinese Journal of Analytical Chemistry
2025;53(7):1108-1117
- CountryChina
- Language:Chinese
-
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.
