CN112480080B - Fluorescent probe for visual detection of silver ions and 2,4, 6-trinitrophenol, preparation method and application - Google Patents

Fluorescent probe for visual detection of silver ions and 2,4, 6-trinitrophenol, preparation method and application Download PDF

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CN112480080B
CN112480080B CN202011307289.3A CN202011307289A CN112480080B CN 112480080 B CN112480080 B CN 112480080B CN 202011307289 A CN202011307289 A CN 202011307289A CN 112480080 B CN112480080 B CN 112480080B
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silver ions
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trinitrophenol
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王斌
江帆
马祥梅
马静
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Anhui University of Science and Technology
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Abstract

The invention belongs to the field of fluorescent probe preparation technology and application, and particularly relates to a fluorescent probe for detecting silver ions and 2,4, 6-trinitrophenol. The preparation method of the invention comprises the step of synthesizing the fluorescent probe by taking quinaldic acid, 3' -diaminobenzidine and polyphosphoric acid as raw materials in one step. The fluorescent probe has good selectivity and visual color change for silver ions and 2,4, 6-trinitrophenol, has detection limits of 1.36 mu M and 0.82 mu M respectively, can be used for respectively identifying silver ions and 2,4, 6-trinitrophenol in environmental water bodies or soil such as tap water, river water and the like, and has good application prospect.

Description

Fluorescent probe for visual detection of silver ions and 2,4, 6-trinitrophenol, preparation method and application
Technical Field
The invention belongs to the technical field of preparation and application of fluorescent probes, and particularly relates to a fluorescent probe for silver ions and 2,4, 6-trinitrophenol, a preparation method and application thereof.
Background
2,4, 6-Trinitrophenol (TNP), also known as picric acid, is one of the powerful explosives in nitroaromatic explosives (NAEs) and is widely used in industry and civilian use, such as fireworks, leather and dyes in the chemical industry. The method has the advantages that the method causes huge pollution to soil and water environments in the production, use and transportation processes, and is a potential soil and water system pollutant.
The fluorescent probe has certain advantages in the aspects of rapidness, accuracy, convenience, economy and the like. In recent years, there have been many reports about recognition of TNP by fluorescent probes, such as fluorescent conjugated polymers, small-molecule fluorophores, metal-organic frameworks, and aggregation-induced luminescent materials. The small molecular organic fluorescent probe has the advantages of high sensitivity, good selectivity, rapidness, convenience, real-time monitoring and the like, and is widely paid attention to a plurality of scientists at home and abroad. However, the currently reported small molecule TNP sensors still have the defects of too long synthetic route, low yield and the like, and the practical application of the small molecule TNP sensors is greatly limited.
Silver materials are widely used in electronics, light industry, pharmaceutical industry and the like, and the produced industrial wastewater releases a large amount of silver ions into the environment. Silver ions are therefore a widely distributed environmental contaminant that, even at low concentrations, can cause serious and permanent poisoning to the environment and humans.
For Ag + The traditional detection method mainly comprises a flame atomic absorption spectrometry, a graphite furnace atomic absorption spectrometry, an inductively coupled plasma atomic emission spectrometry, an electrochemical analysis method and the like. However, the above methods generally have the defects of complex operation, time consumption, expensive equipment and the like, so that the practical application of the methods is greatly limited, and meanwhile, the detection sensitivity and selectivity are still to be improved.
Many fluorescent probes for the separate detection of silver ions and 2,4, 6-trinitrophenol have been previously reported. However, there are few reports that a probe material can be detected visually with high selectivity and high sensitivity in an aqueous environment.
Therefore, a small molecular fluorescent probe which is simple in synthesis, high in yield, high in selectivity and sensitivity, capable of detecting silver ions and 2,4, 6-trinitrophenol TNP in water and soil environment is developed, and has a good application prospect.
The fluorescent probe can be synthesized by one-step reaction, and the sources of the used raw materials are wide, special treatment is not needed before the fluorescent probe is used, the price is low, and the yield is up to more than 80 percent.
Disclosure of Invention
The technical problem to be solved by the invention is to utilize an organic small molecular fluorescent probe which is simple to synthesize and high in yield to be respectively applied to the visual detection of silver ions and 2,4, 6-trinitrophenol in a water body environment.
In order to achieve the above purpose, the invention adopts the following technical scheme:
specifically, the invention provides a fluorescent probe L for detecting silver ions and 2,4, 6-trinitrophenol, which has the following structure:
Figure BDA0002788685080000021
a fluorescence detection method for silver ions and 2,4, 6-trinitrophenol comprises the following steps:
the synthesis method of the fluorescent probe for detection comprises the following steps: 3,3' -diamino benzidine, quinaldine acid and polyphosphoric acid are stirred and mixed uniformly. Then heating to 155-165 ℃ and stirring for reaction for 48-50 h, stopping heating, cooling to room temperature, adding deionized water, adjusting the pH value of the mixed solution to be 9-10 by using sodium hydroxide solution, and carrying out suction filtration to obtain brown solid. Recrystallizing with absolute ethanol for 3 times, and drying to obtain the fluorescent probe L.
The concentration of the sodium hydroxide solution is 0.1mol/L, and the sodium hydroxide solution can be added in a dropwise manner.
In the synthesis method, the quinaldic acid and the 3,3' -diaminobenzidine are calculated according to the molar ratio: 3,3' -diaminobenzidine=2.1 to 2.3:1.
in the synthesis method, 3' -diaminobenzidine (mmol): polyphosphoric acid (mL) =1 (4 to 6).
In the synthesis method, the reaction solution is cooled to room temperature and then deionized water is added in the same volume as the polyphosphoric acid.
The invention also provides application of the fluorescent probe in detecting and identifying silver ions and 2,4, 6-trinitrophenol in the environment.
The auxiliary material for the fluorescence detection method of silver ions and 2,4, 6-trinitrophenol is a mixed solvent, wherein the mixed solvent consists of Tetrahydrofuran (THF) and deionized water, and the volume percentage of water in the mixed solvent is 40% -60%.
Dissolving probe L in mixed solvent to obtain a concentration of 10 -3 ～10 -5 The mol/L solution is used as a fluorescence detection material.
The invention has the beneficial effects that:
(1) The mixing of the fluorescent detection material of the present invention with 2,4, 6-trinitrophenol or silver ions can result in significant changes in system color and fluorescence spectrum.
(2) The fluorescent probe has high selectivity to 2,4, 6-trinitrophenol. The mixing of fluorescent detection materials with several other conventional nitroaromatic explosives does not result in significant changes in the system color and fluorescence spectrum.
(3) The fluorescent probe has high selectivity for silver ion detection. The mixing of fluorescent detection materials with several other conventional metal ions does not result in a significant change in the system color and fluorescence spectrum.
The fluorescent probe has good stability and can be stored for a long time.
(4) The fluorescent probe provided by the invention is simple to synthesize, low in cost and beneficial to commercialized popularization and application. The fluorescent probe has good selectivity and visual color change for silver ions and 2,4, 6-trinitrophenol, has detection limits of 1.36 mu M and 0.82 mu M respectively, can be used for respectively identifying silver ions and 2,4, 6-trinitrophenol in environmental water bodies or soil such as tap water, river water and the like, and has good application prospect.
Drawings
FIG. 1 shows the preparation of a probe according to example 1 1 HNMR spectra.
FIG. 2 is a graph of the fluorescence spectral response of some nitroaromatic explosives to the probe material prepared in example 1.
FIG. 3 is a graph showing the fluorescence intensity of the probe material prepared in example 1 and the fluorescence spectral response of 2,4, 6-trinitrophenol at different concentrations.
FIG. 4 is a graph showing the relationship between the concentration of 2,4, 6-trinitrophenol and the fluorescence signal intensity in the probe material prepared in example 1.
FIG. 5 is a graph of fluorescence spectral response of some metal ions to the probe material prepared in example 1.
FIG. 6 is a graph showing fluorescence intensity versus fluorescence spectral response of silver ions at different concentrations for the probe material prepared in example 1.
FIG. 7 is a graph showing the linear relationship between the concentration of silver ions and the fluorescence signal intensity of the probe material prepared in example 1.
Detailed Description
The preparation method, application and spectral properties of the above-mentioned high-sensitivity and high-selectivity fluorescent probe for respectively identifying silver ions and 2,4, 6-trinitrophenol will be described in more detail by means of the following examples.
Example 1:
(1) 2.29g (13.2 mmol) of quinaldic acid, 1.29g (6 mmol) of 3,3' -diaminobenzidine and 25mL of polyphosphoric acid (PPA) are added into a 50mL three-neck flask, stirred and mixed uniformly, heated to react for 48h at 160 ℃, stopped heating, cooled to room temperature and added with 25mL of deionized water. The mixture was adjusted to ph=9 with sodium hydroxide solution and filtered to give a brown solid. Recrystallizing with absolute ethanol for 3 times, and drying to obtain probe L with yield: 83.6%.
Example 2:
(1) 2.39g (13.8 mmol) of quinaldic acid, 1.29g (6 mmol) of 3,3' -diaminobenzidine and 36mL of polyphosphoric acid (PPA) are added into a 100mL three-necked flask, stirred and mixed uniformly, heated to react for 50h at 165 ℃, stopped heating, cooled to room temperature and then added with 36mL of deionized water. The mixture was adjusted to ph=10 with sodium hydroxide solution and filtered to give a brown solid. Recrystallizing with absolute ethanol for 3 times, and drying to obtain probe L with yield: 84.9%.
Example 3:
(1) 2.18g (12.6 mmol) of quinaldic acid, 1.29g (6 mmol) of 3,3' -diaminobenzidine and 24mL of polyphosphoric acid (PPA) are added into a 50mL three-neck flask, stirred and mixed uniformly, heated to react for 48h at 155 ℃, stopped heating, cooled to room temperature and added with 24mL of deionized water. The mixture was adjusted to ph=9 with sodium hydroxide solution and filtered to give a brown solid. Recrystallizing with absolute ethanol for 3 times, and drying to obtain probe L with yield: 81.2%.
And (3) performing nuclear magnetic resonance analysis on the prepared probe L by adopting a nuclear magnetic resonance analyzer, wherein the result is as follows:
1H NMR (400 MHz, DMSO, unit: ppm, as shown in FIG. 1): 7.61-7.79 (m, 6H), 7.95-7.85 (m, 4H), 8.07-8.12 (d, J=8.1 Hz, 2H), 8.17-8.25 (d, J=8.3 Hz, 2H), 8.50-8.63 (m, 4H), δ13.30 (s, 2H).
Example 4:
fluorescence spectral response measurement of conventional nitroaromatic explosives to probe L solution:
the fluorescence spectrum response of the probe to the conventional nitroaromatic explosive is measured in THF-H 2 O(V THF /V Water and its preparation method =5:5) in a mixed solvent, the probe used was the probe sample prepared in example 1. The probe was prepared with the mixed solvent at a concentration of 10 -4 The mol/L solution is reserved for standby, and the mixed solvent is used for preparing the solution with the concentration of 10 respectively -3 mol/L of 4-nitrotoluene (4-NT), 2, 6-dinitrotoluene (2, 6-DNT), trinitrotoluene (TNT), 2, 4-dinitrotoluene (2, 4-DNT), p-nitrophenol (4-NP), o-nitrophenol (2-NP), nitrobenzene (NB), 2-nitrotoluene (2-NT), 2,4, 6-Trinitrophenol (TNP) were used in the examples below.
In the case of fluorescence detection (λex=369 nm), each nitro compound was added to an equal volume of the probe solution, and the blank was prepared by adding an equal volume of the mixed solvent to the probe solution, and the excitation wavelength for detection was 369nm and the grating slit was 5nm. FIG. 2 is a diagram showing the detection of several conventional nitroaromatic explosives by the probe L molecules.
As can be seen from FIG. 2, the fluorescence emission spectrum of the TNP-added solution showed a significant change in intensity decrease. And the color of the system is converted from light blue to dark green under 365nm ultraviolet light; the other conventional nitroaromatic explosives have little influence on the fluorescence intensity of the probe solution, and the color of the system is basically unchanged under 365nm ultraviolet light. This is because quinoline compounds have a conjugated system with a larger pi bond system, are easy to undergo pi-pi electron transition, combine with TNP molecules with strong electron deficiency through electron transfer, and simultaneously, the N-H bond in the benzimidazole molecules can react with-OH in the TNP molecules through hydrogen bonds to cause fluorescence quenching.
Example 5: fluorescence titration of TNP to fluorescent probe L solution
2mL of the solution was removed by a pipette at a concentration of 10 -4 Transferring the mol/L fluorescent probe L solution into a cuvette, and dripping the solution with the concentration of 10 -3 The effect of TNP concentration on the fluorescence properties of the probe solution was measured with a mol/L TNP solution, and the results are shown in FIG. 3. With the gradual addition of TNP, the intensity of the fluorescence emission peak of the system gradually decreases.
All experimental conditions and treatment methods of the present example only ensure that the TNP concentration in the detection system is different, the fluorescence intensity is measured, and a linear relationship diagram (shown in FIG. 4) of the change of the fluorescence intensity with the TNP concentration is drawn. The analysis experiment result can determine that the probe L has very high sensitivity to TNP, the detection limit is calculated to be 1.36 mu M, and the TNP concentration is calculated to be (20-50) multiplied by 10 -7 The fluorescence intensity between mol/L shows good linear relation.
From the above analysis results, it was found that the fluorescent probe L can efficiently detect TNP.
Example 6: fluorescence spectral response measurement of common metal ions to probe L solution.
The fluorescence spectrum response of the probe to common metal ions is measured in THF/H 2 O(V THF /V Water and its preparation method =5: 5) The probe used was the probe sample prepared in example 1, performed in a mixed solvent. The probe was prepared with the mixed solvent at a concentration of 10 -4 The mol/L solution is reserved for standby, and the mixed solvent is used for preparing the solution with the concentration of 10 respectively -3 mol/L Zn (NO) 3 ) 2 、Fe(NO 3 ) 3 、Cr(NO 3 ) 3 、Co(NO 3 ) 2 、AgNO 3 、Cu(NO 3 ) 2 、Al(NO 3 ) 3 、Mg(NO 3 ) 2 The solutions were used in the following examples.
In performing fluorescence detection, each nitrate solution was added to an equal volume of probe solution. The blank sample is prepared by adding the probe solution into the mixed solvent with equal volume, and the detected excitation wavelength is 369nm and the grating slit is 5nm. FIG. 5 is a diagram showing the detection of several common metal ions by the probe L.
As can be seen from FIG. 5, agNO was added 3 The fluorescence emission spectrum of the probe solution of the solution is obviously weakened and changed. And the color of the system is converted from light blue to dark green under 365nm ultraviolet light; while other nitrate solutions have less influence on the fluorescence intensity of the probe solution, and the color of the system is basically unchanged under 365nm ultraviolet light. The nitrogen atom has stronger chelation to metal ions, and quinoline and imidazole containing the nitrogen atom are good metal chelating agents and can carry out coordination reaction with specific metals, so that the electronic arrangement of fluorophores is changed, and the fluorescence property is changed.
Example 7: agNO 3 Fluorescence titration of solution to fluorescent probe Lsolution
2mL of the solution was removed by a pipette at a concentration of 10 -4 Transferring the mol/L fluorescent probe L solution into a cuvette, and dripping the solution with the concentration of 10 -3 mol/L AgNO 3 The effect of silver ion concentration on the fluorescence properties of the probe solution was tested, and the results are shown in FIG. 6. With AgNO 3 The intensity of fluorescence emission peak of the system is gradually reduced by gradually adding the solution.
All experimental conditions and treatment methods in this example are only to ensure AgNO in the detection system 3 The fluorescence intensity of the solution is measured according to the concentration difference of the solution, and the fluorescence intensity is plotted with AgNO 3 A linear graph of the concentration change of the solution (shown in fig. 7). The analysis experiment result can determine that the probe L has very high sensitivity to silver ions, the calculated detection limit is 0.82 mu M, and the concentration of silver ions is (20-50) multiplied by 10 -7 The fluorescence intensity between mol/L shows good linear relation.
From the above analysis results, it was found that the fluorescent probe L can realize efficient detection of silver ions.

Claims (2)

1. A fluorescent probe detection method for silver ions is characterized in that: the structural formula of the fluorescent probe is as follows:
Figure QLYQS_1
；
the auxiliary material of the fluorescent probe solution state detection mode is a mixed solvent, and the fluorescent probe is dissolved in the mixed solvent to prepare the fluorescent probe solution with the concentration of 10 -3 ~10 -5 The mol/L solution is used as a fluorescence detection material;
the mixed solvent consists of tetrahydrofuran and deionized water, and the volume percentage of water in the mixed solvent is 40% -60%.
2. The method for detecting silver ions by using the fluorescent probe according to claim 1, wherein: the tetrahydrofuran/water solution of the fluorescent probe can selectively detect silver ions at room temperature, and the detection wavelength is 365nm under ultraviolet light.
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Chu-Ming Pang.A dual-channel sensor containing multiple nitrogen heterocycles for the selective detection of Cu2+, Hg2+ and Zn2+ in same solvent system by different mechanism..Dyes and Pigments.2019,第170卷第2页Scheme 1、第1栏倒数第1-2段；第3页第1栏倒数1-2段、以及图1、图2；第7页图10. *
Jiang, Kai.A functionalized fluorochrome based on quinoline-benzimidazole conjugate: From facile design to highly sensitive and selective sensing for picric acid.Dyes and Pigments .2019,第162卷第368页第1栏第3段；第369页Scheme 1；第372页第2栏第3段；第373页图10、图11，第373页第2栏第2段. *

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