CN112409292B - Multifunctional fluorescent probe, preparation method and application - Google Patents
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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Abstract
The invention belongs to the technical field of chemical analysis, and particularly relates to a method for analyzing a sampleThe fluorescent probe is prepared by performing an aldehyde-amine condensation reaction on 4-formyl triphenylamine and 2-hydrazino benzothiazole according to a certain proportion under a certain condition, the synthetic process only needs one step, the reaction condition is mild, and the post-treatment is relatively simple. The synthesized molecular probe can respectively recognize Cu under three conditions2+、Fe3+And Zn2+. The method comprises the following steps: identification of Cu by colorimetric method2+(ii) a Identification of Fe by blue fluorescence brightening in acetonitrile solution3+(ii) a Identification of Zn by green fluorescence in aqueous system2+. The molecular probe has good selectivity for identifying the three ions under different conditions, strong anti-interference capability and low detection limit, can solve the problems of complex synthesis, low efficiency and high cost caused by synthesizing one probe for identifying one ion, and has good application prospect in the fields of environmental engineering and ion detection.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry of metal ion detection, and particularly relates to a multifunctional fluorescent probe, and a preparation method and application thereof.
Background
Copper is a trace heavy metal element necessary for the living body, plays an important role in basic physiological processes, such as acting as an essential cofactor of various enzymes, promoting erythropoiesis, maintaining the health of the central nervous system, and the like, but excessive copper can damage the liver and the kidney, cause neurodegenerative diseases, and has biohazard. Iron, the most abundant transition metal in biological systems, is involved in many physiological processes, such as cellular metabolism, oxygen transport, enzymatic reactions, protein transport, etc., however, the lack or excessive accumulation of iron may affect the normal operation of organisms, causing various health problems. Zinc is the second most abundant transition metal element in the human body and is widely usedAre distributed in cells and body fluids of human bodies, participate in a plurality of metabolic processes, and can cause diseases such as growth arrest, diarrhea, immune system dysfunction, toxic symptoms and the like due to insufficient or excessive intake. Therefore, from the viewpoint of human health, rapid, sensitive and convenient Cu is developed2+、Fe3+And Zn2+The identification method is imperative.
In recent years, fluorescent probes have attracted more and more attention because of their advantages of high selectivity, high sensitivity, fast response time, low cost, etc. The currently reported probes mostly focus on Cu2+、Fe3+And Zn2+The single ion is identified and detected, and the single probe has the problems of complex synthesis, low efficiency, high cost and the like. Therefore, a sensitive and efficient Cu capable of being identified is developed2+、Fe3+And Zn2+The multifunctional fluorescent probe has wide application prospect.
Disclosure of Invention
The present invention is to solve the above problems and to provide a Cu-recognizable package2+、Fe3+And Zn2+A multifunctional fluorescent probe, a preparation method and application. The fluorescent probe can realize the aim of Cu in an acetonitrile solution system2+Colorimetric identification and for Fe3+Fluorescence recognition of Zn in aqueous solution system2+The fluorescent recognition of (2) has better selectivity and sensitivity.
In order to achieve the purpose, the invention adopts the following technical scheme:
a multifunctional fluorescent probe has a structure shown in (I):
a preparation method of a multifunctional fluorescent probe comprises the following specific steps: in an absolute ethanol solution, heating and refluxing 4-formyl triphenylamine and 2-hydrazinobenzothiazole in absolute ethanol to perform an aldehyde-amine condensation reaction; and after the reaction is finished, cooling to room temperature, filtering the precipitate, washing with absolute ethyl alcohol for multiple times, and drying for purification to obtain the multifunctional fluorescent probe.
Further, the feeding molar ratio of the 4-formyl triphenylamine to the 2-hydrazinobenzothiazole is 1: 1.2.
further, the heating reflux time was 3 hours.
Application of multifunctional fluorescent probe in detecting Cu in acetonitrile solution system2+、Fe3+The identified application.
Further, the identification method specifically comprises the following steps: the fluorescent probe is used for detecting Cu in an acetonitrile solution system2+、Fe3+The identification method comprises the following steps: the compound (I) was prepared as an acetonitrile solution and diluted with acetonitrile and observed: if the solution color appears red under the sunlight, Cu is identified2+Presence of (a); if the fluorescence color of the solution is blue under an ultraviolet lamp, Fe is identified3+Presence of (a); if the solution under the fluorescent lamp and the ultraviolet lamp is not changed, Cu is not identified2+And Fe3+Is present.
Application of multifunctional fluorescent probe in water solution system to Zn2+The identified application.
Further, the identification method specifically comprises the following steps: the fluorescent probe is used for detecting Zn in an aqueous solution system2+The identification method comprises the following steps: said compound (I) was prepared as an acetonitrile solution and diluted with water and observed: under an ultraviolet lamp, if the fluorescence of the solution is green, Zn is identified2+Presence of (a); no fluorescence under UV lamp, no Zn was identified2+Is present.
Compared with the prior art, the invention has the following advantages:
(1) the synthesis process of the probe only needs one step, the reaction condition is mild, and the post-treatment is relatively simple;
(2) the probe can realize the reaction of Cu in an acetonitrile solution system2+Colorimetric identification and for Fe3+Fluorescence recognition of Zn in aqueous solution system2+The fluorescence identification is good in selectivity and strong in anti-interference capability;
(3) probe pair Cu2+、Fe3+And Zn2+Identified detection limit is low: cu2+The detection limit is 0.48 mu M, Fe3+The detection limit is 3.2 mu M, Zn2+The limit of detection was 3.2. mu.M.
Drawings
FIG. 1 is a diagram of an ultraviolet spectrum of a probe added with different metal ions in an acetonitrile solution system;
FIG. 2 is a fluorescence spectrum of a probe added with different metal ions in an acetonitrile solution system;
FIG. 3 is a photograph showing the response of a probe after adding different metal ions into an acetonitrile solution system;
FIG. 4 is a fluorescence spectrum of a probe added with different metal ions in an aqueous solution system
FIG. 5 is a photograph showing the response of a probe after adding different metal ions into an aqueous system
FIG. 6 shows probe to Cu in the presence of other metal ions2+Detecting a response graph;
FIG. 7 shows the probe for Fe in the presence of other metal ions3+Detecting a response graph;
FIG. 8 shows the probe for Zn in the presence of other metal ions2+Detecting a response graph;
FIG. 9 shows the probe with Cu added at different concentrations2+Ultraviolet spectrogram of (1);
FIG. 10 shows the addition of different concentrations of Fe to the probe3+A fluorescence spectrum of (a);
FIG. 11 shows the probe with Zn added at different concentrations2+Fluorescence spectrum of (2).
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A multifunctional fluorescent probe has a structure shown in (I):
a preparation method of a multifunctional fluorescent probe comprises the following specific steps: in an absolute ethanol solution, heating and refluxing 4-formyl triphenylamine and 2-hydrazinobenzothiazole in absolute ethanol to perform an aldehyde-amine condensation reaction; and after the reaction is finished, cooling to room temperature, filtering the precipitate, washing with absolute ethyl alcohol for multiple times, and drying for purification to obtain the multifunctional fluorescent probe.
The synthetic route of the fluorescent probe is specifically as follows:
further, the feeding molar ratio of the 4-formyl triphenylamine to the 2-hydrazinobenzothiazole is 1: 1.2.
further, the heating reflux time was 3 hours.
Application of multifunctional fluorescent probe in detecting Cu in acetonitrile solution system2+、Fe3+The identified application.
Further, the identification method specifically comprises the following steps: the fluorescent probe is used for detecting Cu in an acetonitrile solution system2+、Fe3+The identification method comprises the following steps: the compound (I) was prepared as an acetonitrile solution and diluted with acetonitrile and observed: if the solution color is red under sunlight, Cu is identified2+Presence of (a); if the fluorescence color of the solution is blue under an ultraviolet lamp, Fe is identified3+Presence of (a); if the solution under the fluorescent lamp and the ultraviolet lamp is not changed, Cu is not identified2+And Fe3+Is present.
Application of multifunctional fluorescent probe in aqueous solution systemMiddle pair of Zn2+The identified application.
Further, the identification method specifically comprises the following steps: the fluorescent probe is used for detecting Zn in an aqueous solution system2+The identification method comprises the following steps: said compound (I) was prepared as an acetonitrile solution and diluted with water and observed: under an ultraviolet lamp, if the fluorescence of the solution is green, Zn is identified2+Presence of (a); no fluorescence under UV lamp, no Zn was identified2+Is present.
Example 1: identifying Cu2+、Fe3+And Zn2+Preparation method of multifunctional fluorescent probe
The method comprises the following specific steps: 4-formyl triphenylamine (100mg,0.366mmol) is dissolved in absolute ethyl alcohol (15mL), 2-hydrazinobenzothiazole (73mg,0.439mmol) is added, the mixture is refluxed and stirred for 3 hours, after the reaction is finished, the mixture is cooled to room temperature, precipitate is filtered, the precipitate is washed by absolute ethyl alcohol for multiple times, and light yellow product is obtained after drying, and the yield is 73%.
1H NMR(600MHz,DMSO-d6)δ8.06(s,1H),7.71(s,1H),7.59–7.55(m,2H),7.38–7.32(m,5H),7.28(t,J＝7.7Hz,1H),7.14–7.05(m,8H),6.99–6.95(m,2H).
Example 2: probe to Cu in acetonitrile solution system2+、Fe3+Applications on recognition
Respectively prepared at a concentration of 10-2Al of M3+,Fe3+,Co2+,Mg2+,Ni2+,Ag+,Cu2+,Pb2+,Mn2+,Zn2+,K+,Cd2 +,Hg2+,Cr3+,Ca2+,Na+An aqueous solution.
Preparation of acetonitrile solution of probe prepared in example 1: the probe solution (2.5mM, 100. mu.L) was diluted with acetonitrile to a total volume of 10mL, and the prepared metal ion solutions (10. mu.L) were added separately-2M, 10. mu.L) and mixed well. The effect of the addition of different ions on the solution was measured with an ultraviolet spectrophotometer and a fluorescence spectrophotometer as shown in fig. 1 and 2. In FIG. 1, it can be seen that only Cu is present2+Can be added to the probe solution at 505nmA new absorption peak appears, and the solution changes from colorless to red; in FIG. 2, it can be seen that only Fe3+The probe solution has a distinct emission peak at 468nm, and the solution emits blue fluorescence. This is consistent with the photographs of the response of the probe solution of fig. 3 under fluorescent light and ultraviolet light after addition of different ions.
Example 3: probe to Zn in aqueous solution system2+Applications on recognition
An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with water to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10. mu.L) and mixed well. The effect of the addition of different ions on the solution was measured with a steady state fluorescence spectrophotometer. As shown in FIG. 4, it can be seen that only Zn is present2+The addition of the fluorescent probe can lead the probe solution to have a distinct emission peak at 534nm, and the solution emits green fluorescence. This is consistent with the photo of the probe solution of FIG. 5 after addition of different ions under an ultraviolet lamp.
Example 4: probe to Cu in the presence of other metal ions2+Response to (2)
(1) An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10 μ L), the change in the ultraviolet absorption intensity was tested;
(2) an acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10. mu.L), and Cu was further added2+Solution (10. mu.L) was tested for changes in UV absorbance. The change in intensity at 505nm was recorded and a bar graph as shown in figure 6 was made. In FIG. 6, it can be seen that only Cu is added2+A significant enhancement of the absorption intensity at 505nm is caused and in the presence of other metal ions, Cu2+The addition of (2) still causes an increase in the absorption strength. The experimental result further verifies that the probe is matched with Cu2+The excellent selectivity also indicates the excellent anti-interference capability of the probe.
Example 5: the probe is used for detecting Fe in the presence of other metal ions3+Response to (2)
(1) An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10 μ L), the change in fluorescence intensity was measured;
(2) an acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10. mu.L), and Fe was further added3+The change in fluorescence intensity was measured for the solution (10. mu.L), and a histogram as shown in FIG. 7 was obtained. In FIG. 7, it can be seen that only Fe is added3+A significant increase in fluorescence intensity at 468nm is caused and in the presence of other metal ions, Fe3+The addition of (2) still causes an increase in fluorescence intensity. The experimental result further verifies that the probe is used for Fe3+The excellent selectivity also indicates the excellent anti-interference capability of the probe.
Example 6: the probe is used for Zn in the presence of other metal ions2+Response to (2)
(1) An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with water to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10 μ L), the change in fluorescence intensity was tested;
(2) an acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with water to a total volume of 10mL, and the metal ion solutions (10) prepared in example 2 were added, respectively-2M, 10. mu.L), and Zn was further added2+Solution (10. mu.L) was tested for changes in fluorescence intensity. The change in intensity at 534nm was recorded and a histogram as shown in figure 8 was made. In FIG. 8, it can be seen that only Zn is added2+A significant increase in fluorescence intensity at 534nm is caused and Zn in the presence of other metal ions2+The addition of (2) still causes an increase in fluorescence intensity. The experimental result further verifies that the probe pair Zn2+The excellent selectivity also shows the excellent anti-interference capability of the probe.
Example 7: probes for different concentrations of Cu2+Response to (2)
An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and Cu was added at various concentrations2+The solution (0-3.5g/L,10uL) was tested for changes in UV absorption intensity and a UV absorption spectrum plot as shown in FIG. 9 was made at Cu2+The absorption strength has a good linear relation with the concentration of 0.4-1.8 g/L.
Example 8: probes for different concentrations of Fe3+Response to (2)
An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with acetonitrile to a total volume of 10mL, and Fe was added at various concentrations3+(0-3.0g/L, 10. mu.L), the change in fluorescence intensity was measured, and a fluorescence spectrum was made as shown in FIG. 10 at Fe3+The fluorescence intensity has a good linear relation with the concentration within the range of 1.0-2.6 g/L.
Example 9: probes for different concentrations of Zn2+Response to (2)
An acetonitrile solution (2.5mM, 100. mu.L) of the probe prepared in example 2 was diluted with water to a total volume of 10mL, and Zn was added at various concentrations2+The solution (0-2.5g/L, 10. mu.L) was tested for changes in fluorescence intensity and a fluorescence spectrum as shown in FIG. 11 was made in Zn2+The fluorescence intensity has a good linear relation with the concentration within the range of 0.6-2.0 g/L.
Although only the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the above embodiments, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art, and all changes are encompassed in the scope of the present invention.
Claims (8)
1. A multifunctional fluorescent probe is characterized in that the fluorescent probe has a structure shown in (I):
2. the preparation method of the multifunctional fluorescent probe of claim 1, which is characterized by comprising the following specific steps: in an absolute ethanol solution, heating and refluxing 4-formyl triphenylamine and 2-hydrazinobenzothiazole in absolute ethanol to perform an aldehyde-amine condensation reaction; and after the reaction is finished, cooling to room temperature, filtering the precipitate, washing with absolute ethyl alcohol for multiple times, and drying for purification to obtain the multifunctional fluorescent probe.
3. The method for preparing a multifunctional fluorescent probe according to claim 2, characterized in that: the feeding molar ratio of the 4-formyl triphenylamine to the 2-hydrazinobenzothiazole is 1: 1.2.
4. the method for preparing a multifunctional fluorescent probe according to claim 2, characterized in that: the heating reflux time is 3 h.
5. The use of the multifunctional fluorescent probe of claim 1, characterized in that: the fluorescent probe is applied to Cu in an acetonitrile solution system2+、Fe3+And (5) performing identification.
6. The use of the multifunctional fluorescent probe as claimed in claim 5, wherein the fluorescent probe is used for detecting Cu in acetonitrile solution system2+、Fe3+The identification method comprises the following steps: preparing said compound (i) into acetonitrile solution, diluting with acetonitrile, observing: if the solution color is red under sunlight, Cu is identified2+Presence of (a); if the fluorescence color of the solution is blue under an ultraviolet lamp, Fe is identified3+Presence of (a); if the solution under the fluorescent lamp and the ultraviolet lamp is not changed, Cu is not identified2+And Fe3+Is present.
7. The use of the multifunctional fluorescent probe according to claim 1, wherein: said multiple functionsApplication of fluorescent probe in aqueous solution system to Zn2+And (5) performing identification.
8. The use of the multifunctional fluorescent probe of claim 7, wherein the fluorescent probe is used for Zn in an aqueous system2+The identification method comprises the following steps: said compound (I) was prepared as an acetonitrile solution and diluted with water and observed: under an ultraviolet lamp, if the fluorescence of the solution is green, Zn is identified2+Presence of (a); no fluorescence under UV lamp, no Zn was identified2+Is present.
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