CN110818616A - Fluorescent probe for identifying thiocyanate radical and preparation method and detection method thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for identifying thiocyanate radicals, and a preparation method and a detection method thereof. The preparation method comprises (1) adding 1, 2-di- (4-bromophenyl) -1, 2-stilbene, 4-pyridine boric acid and palladium acetate into triethylamine, mixing, and reacting to obtain product A; (2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B; (3) washing the product B to obtain product C; (4) standing and layering the product C, separating the dichloromethane layer at the lowest layer, drying, spin-drying, and recrystallizing with ethanol to obtain product D; (5) and (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane, heating to 75-85 ℃, reacting for 20-36h, adding diethyl ether into the reaction solution until the diethyl ether is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the fluorescent probe. Detecting thiocyanate radicals in a water system. The probe can detect thiocyanate, and has the advantages of low detection cost, simple operation, visual structure, high sensitivity and good selectivity.
Description
Technical Field
The invention relates to a fluorescent probe and a preparation method and application thereof, in particular to a fluorescent probe for identifying thiocyanate radicals and a preparation method and a detection method thereof.
Background
Thiocyanide is used as an important chemical raw material and widely used in the fields of textile printing and dyeing, fine chemical industry, pharmaceutical industry and the like. In the process of preparing industrial products, the adding proportion is excessive and can not completely react, so that a large amount of thiocyanate enters a waste water system. According to the related research, the stability of thiocyanate radical ion is poor, and SCN in waste water-The wastewater is easy to react with oxidants such as chlorine and the like to generate highly toxic cyanogen chloride or be oxidized into cyanide, so that the toxicity of the wastewater is increased; simultaneous SCN-The product has toxicity, and excessive intake of thiocyanate can prevent the use of iodine element by human body and cause acute poisoning of human body. SCN-Has strong coordination and is easy to react with Fe in water3+、Cu2+The metal ions are subjected to a complex reaction to generate a metal complex, so that the chromaticity of the wastewater is increased. The large amount of the waste water containing the thiocyanide enters the water body, which causes pollution to the environment and poses serious threats to the health of human beings and the life of livestock and fishes.
The detection methods of thiocyanate radical reported in the literature include cathode stripping voltammetry, GC-MS and ion chromatography, and the application of the method to the detection of thiocyanate radical in dairy products is rarely reported. In these detection methods, derivatization is required for all methods except ion chromatography, and the operation is complicated. Although these methods have high sensitivity, they have the disadvantages of high detection cost, complex sample processing, time consuming, and unsuitability for real-time and on-site detection. Since fluorescent probes have absolute advantages in terms of selectivity, detection cost, and the like, designing and using fluorescent probes to detect thiocyanate radicals has attracted extensive attention of analysts. The design and synthesis of the fluorescent probe with selectivity to thiocyanate radical can realize the visual detection of thiocyanate radical, so that the high-efficiency and accurate detection method has important significance in the fields of environment, medicine and biology.
Disclosure of Invention
The invention aims to provide a fluorescent probe for identifying thiocyanate radicals, and a preparation method and a detection method thereof. The probe can detect thiocyanate, and has the advantages of low detection cost, simple operation, visual structure, high sensitivity and good selectivity.
The technical scheme of the invention is as follows: a fluorescent probe for identifying thiocyanate radical, wherein the molecular formula of the probe is as follows: c40H52Br2N2The structural formula is shown in figure 1.
The preparation method of the fluorescent probe for identifying thiocyanate radicals comprises the following steps:
(1) adding 1, 2-di- (4-bromophenyl) -1, 2-stilbene, 4-pyridine boric acid and palladium acetate into triethylamine for mixing, and sealing the mixture in N2Reacting for 18-32h at the temperature of 100-120 ℃ in a high-pressure reaction bottle under the atmosphere to obtain a product A;
(2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B;
(3) washing the product B with water and saturated saline solution sequentially to obtain product C;
(4) standing and layering the product C, separating the dichloromethane layer at the lowest layer, drying with anhydrous magnesium sulfate, spin-drying, and recrystallizing with ethanol to obtain product D;
(5) and (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane, heating to 75-85 ℃, reacting for 20-36h, adding diethyl ether into the reaction solution until the diethyl ether is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the fluorescent probe.
In the preparation method of the fluorescent probe for identifying thiocyanate, in the step (1), 150mg of 1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 100mg of 4-pyridineboronic acid and 30mg of palladium acetate are added to each 10mL of triethylamine.
In the preparation method of the fluorescent probe for identifying thiocyanate, in the step (3), the product B is washed with water and saturated saline solution for 3 times.
In the preparation method of the fluorescent probe for identifying thiocyanate, in the step (4), absolute ethyl alcohol is used for recrystallization.
In the preparation method of the fluorescent probe for identifying thiocyanate, in the step (5), the mass ratio of the D product to the 1-bromooctane is 1:2, the reaction temperature is 80 ℃, and the reaction time is 24 hours.
The method for detecting thiocyanate by using the fluorescent probe for identifying thiocyanate is used for detecting thiocyanate in a water system.
The method for detecting thiocyanate by using the fluorescent probe for identifying thiocyanate includes the steps of dissolving the probe in DMSO, diluting the probe with secondary water to obtain a fluorescent reagent, dripping a sample to be identified into the reagent to obtain a sample solution, carrying out fluorescence excitation on the sample solution, and testing and analyzing fluorescence wavelength excited by fluorescence.
In the method for detecting thiocyanate by using fluorescent probe for identifying thiocyanate, the concentration of the probe in the fluorescent reagent is 10-5mol.L-1The fluorescence excitation wavelength is 382nm, and when the sample to be identified is added and thiocyanate is identified, the maximum fluorescence emission wavelength of the reagent is shifted from 485nm to 587 nm.
The invention has the advantages of
The fluorescent probe can identify and detect thiocyanate radicals, is low in cost in the detection process and simple to operate, and the result can be directly seen through fluorescence change, so that the fluorescent probe has the advantage of visualization; in addition, the probe of the invention has the advantages of strong anti-interference capability, high detection sensitivity and good selectivity.
To further illustrate the beneficial effects of the present invention, the inventors made the following experiments:
first, qualitative analysis test
1. In the concentration range of 10-6～10-4In mol/L fluorescent probe water solution, when the excitation wavelength is 382nm, the maximum emission wavelength of the fluorescent probe is 485nm, and when SCN is added into the fluorescent probe water solution-The maximum emission wavelength of the fluorescent probe then shifted from 485nm red to 587nm, which appears as an orange-red fluorescence.
Second, quantitative analysis test
1. The preparation method of the fluorescent probe solution comprises the following steps: 6.08mg of the probe was weighed, dissolved in DMSO, and prepared to a volume of 10mL and a concentration of 1.0X 10-3mol·L-1Taking 1 100.0mL volumetric flask, taking 1mL of the prepared probe solution in the volumetric flask, diluting with secondary water to the scale mark to obtain a solution with a concentration of 1.0X 10-5mol·L-1The probe solution of (1).
2. Weighing superior pure mercuric perchlorate and cadmium perchlorate to prepare 10mL of aqueous solution with the concentrations of 1.0 multiplied by 10- 1mol·L-1And diluting with secondary water step by step according to the requirement.
3. Taking fluorescent reagent 1.0 × 10-5mol·L-1The standard solution was prepared by adding 3mL of a fluorescent reagent to a cuvette and adding 1.0X 10 of the fluorescent reagent dropwise-3mol·L-1SCN-And introducing a fluorescence spectrum into the ionic solution for measurement, wherein the excitation wavelength is 382 nm.
4. Respectively with SCN-The ion concentration is the abscissa, and the fluorescence intensity is the ordinate, to obtain the working curve.
5. And (3) sample determination: two 10.0mL volumetric flasks were taken and added with a fluorescent reagent of 1.0X 10-3mol·L-10.1mL of standard solution, SCN was added to each of the two volumes-Diluting the ionic solution to a scale, standing at room temperature for 5 minutes, introducing a quartz cuvette of 3.0cm for fluorescence measurement, and finding out the concentration of the sample on a working curve according to the fluorescence intensity. The lowest concentration value of detection identification is 3.853 multiplied by 10-8mol·L-1。
Drawings
FIG. 1 is a chemical structural formula of a fluorescent probe;
FIG. 2 is a nuclear magnetic hydrogen spectrum of a fluorescent probe;
FIG. 3 is a graph of fluorescence spectra of fluorescent probes with different metal ions;
FIG. 4 is a graph showing the change in fluorescence of a fluorescent probe in water with the addition of thiocyanate;
FIG. 5 is a graph of the fit of the detection limits of fluorescent probes in detecting thiocyanate radicals.
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Examples of the invention
Example 1, a fluorescent probe for identifying thiocyanate groups, the molecular formula of the probe is: c40H52Br2N2The structural formula is shown in figure 1. The preparation method comprises the following steps:
(1)1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 4-pyridineboronic acid, palladium acetate were added to triethylamine to mix (150 mg of 1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 100mg of 4-pyridineboronic acid, 30mg of palladium acetate were added per 10mL of triethylamine), and the mixture was sealed in N2Reacting the product A in a high-pressure reaction bottle at 110 ℃ for 24 hours under the atmosphere;
(2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B;
(3) washing the product B with water and saturated saline solution for 3 times to obtain product C;
(4) standing and layering the product C, separating the lowest dichloromethane layer, drying with anhydrous magnesium sulfate, spin drying, and recrystallizing with anhydrous ethanol to obtain product D.
(5) And (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane (the mass ratio of the D substance to the 1-bromooctane is 1:2), heating to 80 ℃, reacting for 24 hours, adding diethyl ether into the reaction liquid until the reaction liquid is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the probe.
The method for detecting thiocyanate radical by using the fluorescent probe comprises the steps of dissolving the probe in DMSO, and then diluting with secondary water to the concentration of 10-5mol.L-1Obtaining a fluorescent reagent, then dripping a sample to be identified into the reagent to obtain a sample solution, carrying out fluorescence excitation on the sample solution by using the fluorescence excitation wavelength of 382nm, and when SCN is identified-The maximum fluorescence emission wavelength of the reagent is shifted from 485nm to 587 nm.
Practice ofExample 2, a fluorescent probe for identifying thiocyanate, the molecular formula of the probe is: c40H52Br2N2The structural formula is shown in figure 1. The preparation method comprises the following steps:
(1)1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 4-pyridineboronic acid, palladium acetate were added to triethylamine to mix (150 mg of 1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 100mg of 4-pyridineboronic acid, 30mg of palladium acetate were added per 10mL of triethylamine), and the mixture was sealed in N2Reacting the product A in a high-pressure reaction bottle at 100 ℃ for 32 hours under the atmosphere;
(2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B;
(3) washing the product B with water and saturated saline solution for 3 times to obtain product C;
(4) standing and layering the product C, separating the lowest dichloromethane layer, drying with anhydrous magnesium sulfate, spin drying, and recrystallizing with anhydrous ethanol to obtain product D.
(5) And (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane (the mass ratio of the D substance to the 1-bromooctane is 1:2), heating to 85 ℃, reacting for 20 hours, adding diethyl ether into the reaction solution until the mixture is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the probe.
The method for detecting thiocyanate radical by using the fluorescent probe comprises the steps of dissolving the probe in DMSO, and then diluting with secondary water to the concentration of 10-5mol.L-1Obtaining a fluorescent reagent, then dripping a sample to be identified into the reagent to obtain a sample solution, carrying out fluorescence excitation on the sample solution by using the fluorescence excitation wavelength of 382nm, and when SCN is identified-The maximum fluorescence emission wavelength of the reagent is shifted from 485nm to 587 nm.
Example 3, a fluorescent probe for identifying thiocyanate groups, the molecular formula of the probe is: c40H52Br2N2The structural formula is shown in figure 1. The preparation method comprises the following steps:
(1)1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 4-pyridineboronic acid, palladium acetate were added to triethylamine and mixed (150 mg of 1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 100mg of palladium acetate per 10mL of triethylamine4-pyridine boronic acid, 30mg palladium acetate), sealing the mixture in N2Reacting the product A for 18 hours at 120 ℃ in a high-pressure reaction bottle in the atmosphere;
(2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B;
(3) washing the product B with water and saturated saline solution for 3 times to obtain product C;
(4) standing and layering the product C, separating the lowest dichloromethane layer, drying with anhydrous magnesium sulfate, spin drying, and recrystallizing with anhydrous ethanol to obtain product D.
(5) And (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane (the mass ratio of the D substance to the 1-bromooctane is 1:2), heating to 75 ℃, reacting for 36 hours, adding diethyl ether into the reaction liquid until the reaction liquid is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the probe.
The method for detecting thiocyanate radical by using the fluorescent probe comprises the steps of dissolving the probe in DMSO, and then diluting with secondary water to the concentration of 10-5mol.L-1Obtaining a fluorescent reagent, then dripping a sample to be identified into the reagent to obtain a sample solution, carrying out fluorescence excitation on the sample solution by using the fluorescence excitation wavelength of 382nm, and when SCN is identified-The maximum fluorescence emission wavelength of the reagent is shifted from 485nm to 587 nm.
The above description is only for the purpose of illustrating the present invention and the appended claims, and the scope of the present invention is not limited thereto, and any person skilled in the art can substitute or change the technical solution and the inventive concept of the present invention within the technical scope of the present invention.
Claims (9)
1. A fluorescent probe for identifying thiocyanate radicals is characterized in that the molecular formula of the probe is as follows: c40H52Br2N2The structural formula is as follows:
2. the method for preparing a thiocyanate group-identifying fluorescent probe according to claim 1, comprising the steps of:
(1) adding 1, 2-di- (4-bromophenyl) -1, 2-stilbene, 4-pyridine boric acid and palladium acetate into triethylamine for mixing, and sealing the mixture in N2Reacting for 18-32h at the temperature of 100-120 ℃ in a high-pressure reaction bottle under the atmosphere to obtain a product A;
(2) completely dissolving product A in dichloromethane to obtain black suspension to obtain product B;
(3) washing the product B with water and saturated saline solution sequentially to obtain product C;
(4) standing and layering the product C, separating the dichloromethane layer at the lowest layer, drying with anhydrous magnesium sulfate, spin-drying, and recrystallizing with ethanol to obtain product D;
(5) and (3) adding the D substance into N, N-dimethylformamide for dissolving, then adding 1-bromooctane, heating to 75-85 ℃, reacting for 20-36h, adding diethyl ether into the reaction solution until the diethyl ether is completely precipitated, performing suction filtration, washing twice with diethyl ether, and drying to obtain the fluorescent probe.
3. The method for preparing a thiocyanate group-recognizing fluorescent probe according to claim 2, wherein: in the step (1), 150mg of 1, 2-bis- (4-bromophenyl) -1, 2-stilbene, 100mg of 4-pyridineboronic acid and 30mg of palladium acetate were added per 10mL of triethylamine.
4. The method for preparing a thiocyanate group-recognizing fluorescent probe according to claim 2, wherein: in the step (3), the product B is washed for 3 times by water and saturated salt solution in sequence.
5. The method for preparing a thiocyanate group-recognizing fluorescent probe according to claim 2, wherein: in the step (4), anhydrous ethanol is adopted for recrystallization.
6. The method for preparing a thiocyanate group-recognizing fluorescent probe according to claim 2, wherein: in the step (5), the mass ratio of the D product to the 1-bromooctane is 1:2, the reaction temperature is 80 ℃, and the reaction time is 24 hours.
7. A method for detecting thiocyanate groups using the fluorescent probe for identifying thiocyanate groups according to claim 1, wherein: detecting thiocyanate radicals in a water system.
8. The method for detecting thiocyanate radical by using fluorescent probe for identifying thiocyanate radical as set forth in claim 7, wherein: dissolving a probe in DMSO, diluting with secondary water to obtain a fluorescent reagent, dripping a sample to be identified into the reagent to obtain a sample solution, carrying out fluorescence excitation on the sample solution, and testing and analyzing the fluorescence wavelength excited by fluorescence.
9. The method for detecting thiocyanate groups by using fluorescent probe for identifying thiocyanate groups according to claim 8, wherein: the concentration of the probe in the fluorescent reagent is 10-5mol.L-1The fluorescence excitation wavelength is 382nm, and when the sample to be identified is added and thiocyanate is identified, the maximum fluorescence emission wavelength of the reagent is shifted from 485nm to 587 nm.
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Citations (4)
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|---|---|---|---|---|
| CN106565721A (en) * | 2016-10-25 | 2017-04-19 | 贵州大学 | Fluorescent reagent for selectively recognizing lysine and methionine and recognition application thereof |
| CN106966962A (en) * | 2017-03-22 | 2017-07-21 | 贵州大学 | A kind of probe and its preparation method and application |
| CN106966961A (en) * | 2017-03-22 | 2017-07-21 | 贵州大学 | A kind of 2,6 2 (4 pyridine ethene) naphthalane hydrocarbon derivatives and its preparation method and application |
| CN110128328A (en) * | 2019-06-13 | 2019-08-16 | 贵州大学 | A kind of fluorescence probe and preparation method thereof identifying molybdenum acid ion and recognition methods |
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2019
- 2019-10-25 CN CN201911026244.6A patent/CN110818616B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565721A (en) * | 2016-10-25 | 2017-04-19 | 贵州大学 | Fluorescent reagent for selectively recognizing lysine and methionine and recognition application thereof |
| CN106966962A (en) * | 2017-03-22 | 2017-07-21 | 贵州大学 | A kind of probe and its preparation method and application |
| CN106966961A (en) * | 2017-03-22 | 2017-07-21 | 贵州大学 | A kind of 2,6 2 (4 pyridine ethene) naphthalane hydrocarbon derivatives and its preparation method and application |
| CN110128328A (en) * | 2019-06-13 | 2019-08-16 | 贵州大学 | A kind of fluorescence probe and preparation method thereof identifying molybdenum acid ion and recognition methods |
Non-Patent Citations (1)
| Title |
|---|
| ZHANG TIAN ET AL.,: "Cyano substitution effect on the emission quantum efficiency in stilbene derivatives: A computational study", 《ORGANIC ELECTRONICS》 * |
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