CN112480080A - 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 PDFInfo
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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 comprises the step of synthesizing the fluorescent probe by taking quinaldinic 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, the detection limit is 1.36 mu M and 0.82 mu M respectively, the fluorescent probe can be used for identifying the silver ions and the 2,4, 6-trinitrophenol in environmental water bodies such as tap water, river water and the like or soil respectively, and the fluorescent probe has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fluorescent probe preparation and application, and particularly relates to a fluorescent probe for silver ions and 2,4, 6-trinitrophenol, a preparation method and application.
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 chemical industries of fireworks, leather, dyes and the like. The pollution to soil and water environment in the process of production, use and transportation is huge, and the pollution 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 of TNP recognition by fluorescent probes, such as fluorescent conjugated polymers, small molecule fluorophores, metal-organic frameworks, and aggregation-induced luminescent materials. The small-molecule organic fluorescent probe has the advantages of high sensitivity, good selectivity, rapidness, convenience, real-time monitoring and the like, and is widely concerned by many 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 the industries of electronics, light industry, pharmacy and the like, and the generated industrial wastewater can release a large amount of silver ions into the environment. Silver ions are therefore a widely distributed environmental pollutant, causing serious and permanent poisoning, even at low concentrations, both to the environment and to humans.
For Ag+The traditional detection methods mainly comprise flame atomic absorption spectrometry, graphite furnace atomic absorption spectrometry, inductively coupled plasma atomic emission spectrometry, electrochemical analysis and the like. However, the above methods generally have the disadvantages of complicated operation, time consumption and expensive equipment, which make them greatly limited in practical application, and at the same time, the sensitivity and selectivity of detection need to be improved.
Many fluorescent probes for the separate detection of silver ions and 2,4, 6-trinitrophenol have been previously reported. However, it has been reported that one probe material can be highly selective, highly sensitive, and visually detectable for both of the above two substances in an aqueous environment.
Therefore, the micromolecule fluorescent probe which is simple to synthesize, high in yield, high in selectivity and sensitivity and capable of detecting silver ions and 2,4, 6-trinitrophenol TNP in water and soil environments is developed, and the micromolecule fluorescent probe has a good application prospect.
The fluorescent probe can be synthesized by one-step reaction, the used raw materials are wide in source, special treatment is not needed before use, the price is low, and the yield is up to more than 80%.
Disclosure of Invention
The invention aims to solve the technical problem that an organic small-molecule fluorescent probe with simple synthesis and high yield is respectively applied to the visual detection of silver ions and 2,4, 6-trinitrophenol in a water body environment.
In order to achieve the 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:
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: stirring and mixing 3,3' -diaminobenzidine, quinaldic acid and polyphosphoric acid uniformly. And then heating to 155-165 ℃, stirring and reacting for 48-50 h, stopping heating, cooling to room temperature, adding deionized water, adjusting the pH of the mixed solution to 9-10 by using a sodium hydroxide solution, and performing suction filtration to obtain a brown solid. And recrystallizing with absolute ethyl alcohol 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, and the ratio of the quinaldic acid: 3,3' -diaminobenzidine 2.1 to 2.3: 1.
in the synthesis method, 3,3' -diaminobenzidine (mmol): polyphosphoric acid (mL) ═ 1 (4-6).
In the synthesis method, the reaction liquid is cooled to room temperature, and then deionized water is added, wherein the volume of the deionized water is the same as that of 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.
An auxiliary material for a 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 the probe L in the mixed solvent to prepare the concentration of 10-3～10-5And using the solution of mol/L as a fluorescence detection material.
The invention has the following beneficial effects:
(1) the fluorescent detection material disclosed by the invention can cause obvious changes of system color and fluorescence spectrum when being mixed with 2,4, 6-trinitrophenol or silver ions.
(2) The fluorescent probe has high selectivity on 2,4, 6-trinitrophenol. The fluorescent detection material cannot cause obvious changes of system color and fluorescence spectrum when being mixed with other conventional nitro-aromatic explosives.
(3) The fluorescent probe has high selectivity for silver ion detection. The fluorescent detection material mixed with several other conventional metal ions cannot cause significant changes in system color and fluorescence spectrum.
The fluorescent probe disclosed by the invention is good in stability and further can be stored and used for a long time.
(4) The fluorescent probe of the invention has simple synthesis and low cost, and is beneficial to commercial popularization and application. The fluorescent probe has good selectivity and visual color change for silver ions and 2,4, 6-trinitrophenol, the detection limit is 1.36 mu M and 0.82 mu M respectively, the fluorescent probe can be used for identifying the silver ions and the 2,4, 6-trinitrophenol in environmental water bodies such as tap water, river water and the like or soil respectively, and the fluorescent probe has good application prospect.
Drawings
FIG. 1 is a schematic diagram showing preparation of a probe in example 11HNMR spectrogram.
FIG. 2 is a graph showing the fluorescence spectrum 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 spectrum response of 2,4, 6-trinitrophenol at different concentrations.
FIG. 4 is a graph of the linear relationship between the concentration of 2,4, 6-trinitrophenol and the intensity of the fluorescence signal for the probe material prepared in example 1.
FIG. 5 is a graph showing the fluorescence spectral response of some metal ions to the probe material prepared in example 1.
FIG. 6 is a graph showing the fluorescence intensity of the probe material prepared in example 1 and the fluorescence spectrum response of silver ions at different concentrations.
FIG. 7 is a graph showing the linear relationship between the concentration of silver ions and the intensity of fluorescence signals in the probe material prepared in example 1.
Detailed Description
The preparation method, the application and the spectral performance of the fluorescent probe for respectively identifying silver ions and 2,4, 6-trinitrophenol with high sensitivity and high selectivity are described in more detail by the following examples.
Example 1:
(1) 2.29g (13.2mmol) of quinaldic acid, 1.29g (6mmol) of 3,3' -diaminobenzidine and 25mL of polyphosphoric acid (PPA) are added into a 50mL three-necked flask, stirred and mixed uniformly, heated to 160 ℃ for stirring reaction for 48h, stopped heating, cooled to room temperature, and then 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 ethyl alcohol for 3 times, and drying to obtain a probe L, wherein the yield is as follows: 83.6 percent.
Example 2:
(1) 2.39g (13.8mmol) of quinaldinic acid, 1.29g (6mmol) of 3,3' -diaminobenzidine and 36mL of polyphosphoric acid (PPA) are added into a 100mL three-necked flask, stirred and mixed uniformly, heated to 165 ℃ for stirring reaction for 50h, stopped heating, cooled to room temperature, and 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 ethyl alcohol for 3 times, and drying to obtain a probe L, wherein the yield is as follows: 84.9 percent.
Example 3:
(1) 2.18g (12.6mmol) of quinaldic acid, 1.29g (6mmol) of 3,3' -diaminobenzidine and 24mL of polyphosphoric acid (PPA) are added into a 50mL three-necked flask, stirred and mixed uniformly, heated to 155 ℃ for stirring reaction for 48h, stopped heating, cooled to room temperature, and then 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 ethyl alcohol for 3 times, and drying to obtain a probe L, wherein the yield is as follows: 81.2 percent.
The prepared probe L was subjected to nmr analysis using an nmr apparatus, and the results were as follows:
1H NMR (400MHz in 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 ═ 8.1Hz,2H),8.17-8.25(d, J ═ 8.3Hz,2H),8.50-8.63(m,4H), delta 13.30(s,2H).
Example 4:
measurement of fluorescence spectrum response of conventional nitroaromatic explosives to a probe L solution:
the fluorescence spectrum response of the probe to the conventional nitroaromatic explosives is measured in THF-H2O(VTHF/VWater (W)5:5) in a mixed solvent, and the probe used was the probe sample prepared in example 1. The probe is prepared by using a mixed solvent with the concentration of 10-4Storing the solution of mol/L for later use, and preparing the solution with the concentration of 10 by using the mixed solvent respectively-3mol/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) was used in each of the following examples.
When fluorescence detection is carried out (lambda ex is 369nm), an equal volume of probe solution is added into each nitro compound, an equal volume of mixed solvent is added into a blank sample probe solution for preparation, the excitation wavelength of detection is 369nm, and the grating slit is 5 nm. Obtaining a diagram 2 which is a diagram of the detection condition of the probe L molecule to several conventional nitroaromatic explosives.
As can be seen from FIG. 2, the fluorescence emission spectra of the TNP-containing solution showed a significant intensity-decreasing change. And the color of the system is converted from light blue to dark green under 365nm ultraviolet light; and 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. The quinoline compound has a conjugated system with a larger pi bond system, is easy to generate pi-pi electron transition and is combined with TNP molecules with strong electron deficiency through electron transfer, and meanwhile, N-H bonds in benzimidazole molecules can cause fluorescence quenching with-OH in TNP molecules through hydrogen bond action.
Example 5: fluorescent titration of fluorescent Probe L solution by TNP
Pipetting 2mL with 10 concentration using pipette-4Transferring the solution of the fluorescent probe L in mol/L into a cuvette, and dropwise adding the solution of the fluorescent probe L in a concentration of 10-3The effect of TNP concentration on the fluorescence properties of the probe solution was tested in 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 procedures in this example were performed to ensure that the concentration of TNP in the assay system was different, the fluorescence intensity was measured, and a linear plot of fluorescence intensity as a function of TNP concentration was prepared (FIG. 4). The result of the analysis experiment can determine that the probe L has high sensitivity to TNP, the detection limit is 1.36 mu M, and the concentration of TNP is (20-50) multiplied by 10-7The fluorescence intensity between mol/L shows a good linear relation.
From the above analysis results, it is known that the fluorescent probe L can realize highly efficient detection of TNP.
Example 6: and (3) measuring the fluorescence spectrum response of the common metal ions to the probe L solution.
The fluorescence spectrum response of the probe to common metal ions is measured in THF/H2O(VTHF/VWater (W)5:5) the probe used was the probe sample prepared in example 1. The probe is prepared by using a mixed solvent with the concentration of 10-4Storing the solution of mol/L for later use, and preparing the solution with the concentration of 10 by using the mixed solvent respectively-3mol/L of Zn (NO)3)2、Fe(NO3)3、Cr(NO3)3、Co(NO3)2、AgNO3、Cu(NO3)2、Al(NO3)3、Mg(NO3)2The solutions were used in the following examples.
In the case of fluorescence detection, each nitrate solution was added to an equal volume of probe solution. The blank sample is prepared by adding equal volume of mixed solvent into probe solution, the detected excitation wavelength is 369nm, and the grating slit is 5 nm. FIG. 5 is obtained, which is a diagram of the detection of several common metal ions by the probe L.
As can be seen from FIG. 5, AgNO was added3The fluorescence emission spectrum of the probe solution of the solution has obvious intensity reduction change. And the color of the system is converted from light blue to dark green under 365nm ultraviolet light; and other nitrate solutions have small influence on the fluorescence intensity of the probe solution, and the color of the system is basically unchanged under 365nm ultraviolet light. The reason is that nitrogen atoms have strong chelation on metal ions, and quinoline and imidazole containing nitrogen atoms are good metal chelating agents and can generate coordination reaction with specific metals, so that the electronic arrangement of a fluorophore is changed, and the fluorescence property is changed.
Example 7: AgNO3Fluorescence titration of solution to solution of fluorescent Probe L
Pipetting 2mL with 10 concentration using pipette-4Transferring the solution of the fluorescent probe L in mol/L into a cuvette, and dropwise adding the solution of the fluorescent probe L in a concentration of 10-3mol/L AgNO3The effect of the silver ion concentration on the fluorescence performance of the probe solution was tested, and the results are shown in FIG. 6. With AgNO3The intensity of the fluorescence emission peak of the system is gradually reduced by gradually adding the solution.
All experimental conditions and treatment methods in this example were only to ensure that AgNO was detected in the system3Measuring the fluorescence intensity of the solution with different concentrations, and plotting the fluorescence intensity along with AgNO3Graph showing the linear relationship of the solution concentration change (fig. 7). The result of the analysis experiment can determine that the probe L has high sensitivity to silver ions, the detection limit is calculated to be 0.82 mu M, and the silver ion concentration is (20-50) multiplied by 10-7The fluorescence intensity between mol/L shows a good linear relation.
From the analysis results, the fluorescent probe L can realize high-efficiency detection on the silver ions.
Claims (9)
1. An optical probe L for detecting silver ions and 2,4, 6-trinitrophenol fluorescence is characterized in that: the structural formula of the fluorescent probe L is as follows:
2. the method for preparing the silver ion and 2,4, 6-trinitrophenol fluorescent probe L according to claim 1 is characterized by comprising the following steps:
step 1): adding 3,3' -diaminobenzidine, quinaldic acid and polyphosphoric acid into a three-neck flask, stirring and mixing uniformly,
step 2): heating to 155-165 ℃, stirring for reaction for 48-50 h, stopping heating, cooling to room temperature, and adding deionized water;
step 3): adjusting the pH value of the mixed solution to 9-10 by using a sodium hydroxide solution, and performing suction filtration to obtain a brown solid;
step 4): and recrystallizing with absolute ethyl alcohol for 3 times, and drying to obtain the fluorescent probe L.
3. The method for preparing the fluorescent probe L for silver ions and 2,4, 6-trinitrophenol according to claim 2, characterized in that: in the step 1), the molar ratio of the quinaldic acid to the 3,3' -diaminobenzidine is 2.1-2.3: 1.
4. the preparation method of the fluorescent probe L for silver ions and 2,4, 6-trinitrophenol according to claim 2, characterized in that: in the step 1), 3,3' -diaminobenzidine: the molar volume ratio of the polyphosphoric acid is 1: 4-6.
5. The preparation method of the fluorescent probe L for silver ions and 2,4, 6-trinitrophenol according to claim 2, characterized in that: in the step 2), the deionized water is added after the temperature is cooled to the room temperature, and the volume of the deionized water is the same as that of the polyphosphoric acid.
6. The method for detecting the silver ions and the 2,4, 6-trinitrophenol by using the fluorescent probe as claimed in claim 1, wherein the method comprises the following steps: the auxiliary material of the solution state detection mode is a mixed solvent, and the probe L is dissolved in the mixed solvent to prepare the solution with the concentration of 10-3～10-5And using the solution of mol/L as a fluorescence detection material.
7. The fluorescence detection method for silver ions and 2,4, 6-trinitrophenol according to claim 6, characterized in that: the mixed solvent consists of tetrahydrofuran and deionized water, and the volume percentage of water in the mixed solvent is 40-60%.
8. The fluorescence detection method for silver ions and 2,4, 6-trinitrophenol according to claim 6, characterized in that: the THF/water solution of the fluorescent probe can selectively detect silver ions and 2,4, 6-trinitrophenol at room temperature under 365nm ultraviolet light.
9. The fluorescence detection method for silver ions and 2,4, 6-trinitrophenol according to claim 6, characterized in that: silver ions or 2,4, 6-trinitrophenol are added into THF/water solution of the fluorescent probe, and the color of the solution is changed from light blue to dark green.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024468A (en) * | 2021-03-23 | 2021-06-25 | 吉林师范大学 | Fluorescent molecular probe for detecting picric acid and preparation method and application thereof |
| CN114479104A (en) * | 2022-01-24 | 2022-05-13 | 辽宁大学 | Reagent for detecting Pi and o-phenylenediamine based on visual series connection and detection method |
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2020
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Non-Patent Citations (2)
| Title |
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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." * |
| JIANG, KAI: "A functionalized fluorochrome based on quinoline-benzimidazole conjugate: From facile design to highly sensitive and selective sensing for picric acid" * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113024468A (en) * | 2021-03-23 | 2021-06-25 | 吉林师范大学 | Fluorescent molecular probe for detecting picric acid and preparation method and application thereof |
| CN113024468B (en) * | 2021-03-23 | 2022-07-12 | 吉林师范大学 | Fluorescent molecular probe for detecting picric acid and preparation method and application thereof |
| CN114479104A (en) * | 2022-01-24 | 2022-05-13 | 辽宁大学 | Reagent for detecting Pi and o-phenylenediamine based on visual series connection and detection method |
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