CN113004172A - Preparation method of AIE fluorescent probe for detecting deltamethrin - Google Patents
Preparation method of AIE fluorescent probe for detecting deltamethrin Download PDFInfo
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- G01N21/64—Fluorescence; Phosphorescence
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Abstract
The invention relates to a preparation method of an AIE fluorescent probe for detecting deltamethrin. The preparation method specifically comprises the following steps: under the protection of nitrogen, mixing the compound 2 and the compound 3, adding the mixture into dry acetonitrile, adding dry potassium carbonate and potassium iodide, stirring, refluxing, reacting for 8-36 hours, evaporating to remove the solvent, adding a proper amount of dichloromethane, neutralizing the potassium carbonate with dilute hydrochloric acid until the pH value is =7, separating an organic layer, concentrating, and separating a product through silica gel column chromatography to obtain the AIE fluorescent probe. The fluorescence of the compound prepared by the invention is obviously changed in the presence of deltamethrin, the detection of deltamethrin is not interfered by the presence of other pesticides, the detection limit is 2.02 mu M, and the compound can be used for selectively and sensitively detecting deltamethrin pesticides and has important practical application value for the detection of pyrethroid pesticides.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and analytical chemistry, and particularly relates to a preparation method of an AIE fluorescent probe for detecting deltamethrin.
Background
Pyrethroid pesticides are the most widely used broad-spectrum insecticides in the world at present. Due to the characteristics of wide insecticidal spectrum, high pesticide effect and low residue, the insecticidal composition is widely applied to prevention and control of agricultural pests and sanitary pests, grain storage and the like. Pyrethroids are not safe pesticides either. Research shows that the pyrethroid pesticide after being enriched in food chain can cause nausea, headache, dizziness, skin irritation and other untoward reactions in human body and has obvious toxic action on human body immunity and cardiovascular disease. Therefore, the method has important significance in detecting the residue of the pyrethroid pesticide in agricultural products and developing a rapid detection technology of the pyrethroid pesticide. At present, the detection technology of the pyrethroid pesticide mainly comprises gas chromatography, high performance liquid chromatography, chromatography-mass spectrometry combined technology, spectrophotometry and the like. The first three types of chromatography are expensive in equipment, complex in sample pretreatment, high in requirements on instrument equipment and operators, and not suitable for rapid field detection. The spectrophotometry is to use a color developing agent to react with pyrethroid molecules and to indirectly determine through detecting products. This method is highly noisy and has low sensitivity and accuracy. Therefore, the development of rapid, simple, convenient, accurate and low-cost pyrethroid pesticide detection technology capable of on-site detection has clear and urgent practical requirements and great economic value.
The fluorescent probe is a novel detection technology which is rapidly developed in recent years, has the advantages of high sensitivity, good selectivity, convenience, rapidness, low cost, no need of pretreatment, capability of field detection and the like, and is deeply valued in the fields of life science, material science, environmental science and the like. In comparison, the organic fluorescent molecule has the advantages of stable structure, convenience in synthesis, low cost, easiness in operation, good sensitivity and selectivity, capability of realizing in-situ detection and the like, and shows good application prospect in the aspect of field real-time detection. However, the traditional organic fluorescent probe is easy to generate aggregation induced fluorescence quenching effect in the water phase, and is not beneficial to detecting the pyrethroid pesticide in the water phase. In recent years, fluorescent probes having Aggregation Induced Emission (AIE) performance have been attracting attention because they emit light efficiently in poor solvents such as water. Moreover, the AIE fluorescent probe also has good environmental adaptability and test object selectivity. Therefore, the organic fluorescent probe capable of sensitively detecting the pyrethroid pesticide in the water phase with high selectivity is constructed by utilizing the characteristic that the AIE fluorescent probe effectively emits light in the water phase, and the method has very important practical significance and application value.
Disclosure of Invention
One purpose of the invention is to provide an AIE fluorescent probe for deltamethrin detection, which can sensitively and selectively detect the existence of deltamethrin through obvious fluorescence quenching and has good application prospect.
The invention relates to an AIE fluorescent probe for detecting deltamethrin, which has the chemical name of (Z) -4- (1-cyano-2-styryl) -phenoxyacetic acid pentaerythrityl tetraacetate (compound 1) and the molecular formula of C73H56N4O12The AIE fluorescent probe is a pentaerythritol tetraester structure with four cyanobenzene AIE structural units at the chain end, and the specific structure is as follows:
another object of the present invention is to provide a method for preparing the fluorescent probe AIE (Compound 1).
The synthetic route of the compound 1 is as follows:
wherein: the compound 2 is hydroxyl cyano stilbene, the compound 3 is chloroacetic acid pentaerythritol tetraester, and the compound 1 is (Z) -4- (1-cyano-2-styryl) -phenoxyacetic acid pentaerythritol tetraester.
The preparation method of the compound (Z) -4- (1-cyano-2-styryl) -phenoxyacetic acid pentaerythritol ester (compound 1) specifically comprises the following steps:
under the protection of nitrogen, mixing a compound 2 and a compound 3 in a molar ratio of 4-6: 1, adding into dry acetonitrile, adding dry potassium carbonate (the molar ratio of the dry potassium carbonate to the compound 2 is 1-3: 1) and potassium iodide (the molar ratio of the potassium iodide to the compound 2 is 0.1-0.5: 1), stirring, refluxing and reacting for 8-36 hours, after the reaction is finished, evaporating the solvent under reduced pressure, adding a proper amount of dichloromethane, neutralizing the potassium carbonate with dilute hydrochloric acid until the pH value is 7, separating an organic layer, concentrating, and separating a product through 200-mesh silica gel column chromatography (an eluent is dichloromethane) to obtain a yellow solid compound 1, namely the AIE fluorescent probe (Z) -4- (1-cyano-2-styryl) -acetic acid pentaerythritol phenoxyl tetraester.
The molecular formula of the AIE fluorescent probe (compound 1) prepared by the invention is C73H56N4O12Nuclear magnetic resonance hydrogen spectrum (400MHz, CDCl)3)δ:7.83-7.86(m,12H,CH and ArH),7.63(d,J＝8.8Hz,8H,ArH),7.47-7.50(m,12H,ArH),7.05(d,J＝8.8Hz,8H,ArH),4.92(s,8H,CH2),4.17(s,8H,CH2) Nuclear magnetic resonance carbon spectrum (100MHz, CDCl)3) Delta ppm 168.65,158.72,141.42,134.32,130.73,129.36,127.65,127.37,118.39,115.54,110.31,64.96,55.35,30.05 MALDI-TOF-Mass Spectrometry (m/s): calculated value C73H56N4O121180.389(M)+Measured value 1181.697[ MH]+,1204.617[MHNa]+。
The AIE fluorescent probe (compound 1) prepared by the invention is light yellow in tetrahydrofuran solution, and has weak blue fluorescence at 445 nm. In a tetrahydrofuran-water (5:95) mixed solution, the probe fluoresces strongly blue at 455nm with an absolute fluorescence quantum yield of 0.81. The fluorescent probe can form a 1:1 complex with deltamethrin in the tetrahydrofuran-water (5:95) mixed solution, fluorescence is obviously quenched, the fluorescence quenching degree is in direct proportion to the deltamethrin concentration in a certain range, and the fluorescent probe can be used for sensitive detection of deltamethrin in the environment and is an ideal deltamethrin rapid detection fluorescent probe.
The hydroxyl cyano stilbene (compound 2) is prepared according to the method of the published literature (Master thesis of Fujian university, Linlian bin, 2018).
The chloracetic acid pentaerythrityl ester (compound 3) is prepared according to the method of the published literature (RSC Advances,2015,5(28): 21865-21876).
Application of AIE fluorescent probe (compound 1) to detection of deltamethrin
The AIE fluorescent probe (compound 1) prepared by the invention is prepared into a solution with a certain concentration, deltamethrin series solutions with gradient concentration are prepared according to the molar multiples of 0, 0.2, 0.4, 0.6, 0.8, 1.0, 2.0, 4.0, 6.0, 8.0, 10, 20, 40, 60, 80 and 100 of the concentration of the compound 1, the compound 1 and the deltamethrin series solutions are respectively and fully shaken and mixed one by one, the fluorescence intensity of mixed solution is measured, and a deltamethrin gradient change standard curve with the deltamethrin concentration as the horizontal coordinate and the mixed solution fluorescence intensity as the vertical coordinate is established.
The compound 1 was mixed with a solution containing deltamethrin pesticide of unknown concentration, and the fluorescence intensity of the mixed solution was measured. And comparing the obtained fluorescence intensity value with the established deltamethrin concentration gradient change standard curve, and reading out the deltamethrin content in the deltamethrin solution with unknown concentration from the curve chart.
The invention has the following beneficial results: the prepared compound 1 has the fluorescence changed remarkably in the presence of deltamethrin, the detection of deltamethrin is not interfered by the presence of other pesticides, the detection limit is 2.02 mu M, and the compound can be used for selectively and sensitively detecting deltamethrin pesticides, and has important practical application value for detecting pyrethroid pesticides in complex environments and real samples.
Drawings
FIG. 1 is a fluorescence emission spectrum of compound 1 mixed with various common pesticide molecules in tetrahydrofuran-water solution;
FIG. 2 is a fluorescence spectrum of compound 1 mixed with deltamethrin of different concentrations in tetrahydrofuran water solution;
FIG. 3 is a standard curve of the gradient change of deltamethrin concentration and the change of fluorescence intensity;
FIG. 4 is a plan view ofIn aqueous solution of hydrofuran, compound 1 is mixed with other interfering pesticide molecules or added with 2X 10- 5A fluorescence ratio diagram of adding deltamethrin to the compound 1 after mixing mol/L deltamethrin;
FIG. 5 is an infrared spectrum of Compound 1, identifying the structure of each functional group of Compound 1;
FIG. 6 is a NMR spectrum of Compound 1, identifying the structure of Compound 1;
FIG. 7 is a NMR carbon spectrum of Compound 1, identifying the structure of Compound 1;
fig. 8 is a mass spectrum of compound 1, identifying the structure of compound 1.
Detailed Description
The following series of specific examples are given to further illustrate the present invention, but the present invention is not limited to these specific examples, and any modification of the present invention that would be obvious to those skilled in the art to achieve similar results would also be included in the present invention.
In fig. 1, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution is 5:95, the abscissa is the wavelength, and the ordinate is the fluorescence intensity. The molar concentration of Compound 1 in the figure is 1X 10-5mol/L, the molar concentration of various common pesticide molecules is 1 multiplied by 10-4mol/L. When various pesticide molecules are tested, the compound has obvious response to the deltamethrin and the fluorescence is remarkably quenched, which shows that the compound 1 can selectively identify the deltamethrin.
In fig. 2, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution was 5:95, the abscissa was the wavelength, and the ordinate was the fluorescence intensity. The molar concentration of Compound 1 was 1X 10-5mol/L, the concentration of deltamethrin is 0, 0.2, 0.4, 0.6, 0.8, 1.0, 2.0, 4.0, 6.0, 8.0, 10, 20, 40, 60, 80 and 100 times of the concentration of the compound 1 in sequence. FIG. 2 shows that the fluorescence intensity of Compound 1 is significantly decreased with increasing concentration of deltamethrin.
In FIG. 3, the concentration of deltamethrin is 0 to 1X 10-5In the mol/L range, the decrease of the fluorescence intensity of the compound 1 and deltamethrin mixed system is in linear relation with the deltamethrin concentration,can be used as a standard working curve for detecting the concentration of the deltamethrin in a contrast way.
In FIG. 4, the volume ratio of tetrahydrofuran to water in the tetrahydrofuran aqueous solution was 5:95, and the ordinate I/I0The meaning of (A) is: i is0The fluorescence intensity of a mixed system after deltamethrin is added into the compound 1, and I is the fluorescence intensity of the mixed system of the compound 1 plus other interfering pesticide molecules or the mixed system of the compound 1 plus deltamethrin plus other interfering pesticide molecules. The molar concentration of Compound 1 was 1X 10-5mol/L, the molar concentration of other interfering pesticide molecules is 2 multiplied by 10-5mol/L. As can be seen from FIG. 4, other pesticide molecules do not interfere with the detection of deltamethrin by the fluorescent probes of the present invention.
Example 1
Under the protection of nitrogen, compound 2(4mmol) and compound 3(1mmol) were added to 50mL of dry acetonitrile, and then dried potassium carbonate (4mmol) and potassium iodide (0.4mmol) were added, and the reaction was stirred under reflux for 36 hours. After the reaction is finished, the solvent is evaporated under reduced pressure, 50mL of dichloromethane is added, potassium carbonate is neutralized by 1M diluted hydrochloric acid until the pH value is 7, an organic layer is separated, the organic layer is concentrated, and a product is separated by 200-mesh silica gel column chromatography (an eluent is dichloromethane) to obtain a yellow solid, namely the AIE fluorescent probe (compound 1) with the molecular formula of C73H56N4O12The yield was 48%.
In this example, compound 2 was prepared according to the published literature (master thesis of fujian faculty university, forest bin, 2018); compound 3 was prepared according to published literature (RSC Advances,2015,5(28): 21865-21876).
According to the technical scheme of the invention, deltamethrin series solutions with gradient concentration are prepared by using the molar multiple of the AIE fluorescent probe (compound 1) prepared in the embodiment, then the deltamethrin series solutions are fully shaken and mixed with the deltamethrin series solutions one by one, and a deltamethrin concentration gradient change standard curve with deltamethrin concentration as an abscissa and deltamethrin fluorescence intensity as an ordinate is established after the fluorescence intensity of the mixed solution is measured. The standard curve of the concentration gradient is shown in FIG. 3.
The standard curve of the concentration gradient change (figure 3) is mixed with the solution containing the deltamethrin pesticide with unknown concentration, and the fluorescence intensity of the mixed solution is measured. And comparing the obtained fluorescence intensity value with a standard curve, and reading out the content of the deltamethrin in the deltamethrin solution with unknown concentration from the curve.
The fluorescence emission spectrum of compound 1 prepared in this example after mixing with various common pesticide molecules is shown in fig. 1.
The fluorescence spectrum of compound 1 prepared in this example mixed with deltamethrin at different concentrations is shown in fig. 2.
The structure of each functional group of compound 1 prepared in this example can be determined by IR spectroscopy as shown in FIG. 5.
The NMR spectrum of compound 1 prepared in this example with a definite structure is shown in FIG. 6.
The NMR spectrum is shown in FIG. 7.
The mass spectrum of the structure of compound 1 prepared in this example is shown in fig. 8.
Example 2
Under the protection of nitrogen, compound 2(5mmol) and compound 3(1mmol) were added to 60mL of dry acetonitrile, and then dried potassium carbonate (10mmol) and potassium iodide (1mmol) were added, and the reaction was stirred under reflux for 20 hours. After the reaction is finished, the solvent is evaporated under reduced pressure, 50mL of dichloromethane is added, potassium carbonate is neutralized by 1M diluted hydrochloric acid until the pH value is 7, an organic layer is separated, the organic layer is concentrated, and a product is separated by 200-mesh silica gel column chromatography (an eluent is dichloromethane) to obtain a yellow solid, namely the AIE fluorescent probe (compound 1) with the molecular formula of C73H56N4O12Yield 66%.
In this example, compound 2 was prepared according to the published literature (master thesis of fujian faculty university, forest bin, 2018); compound 3 was prepared according to published literature (RSC Advances,2015,5(28): 21865-21876).
Example 3
Under the protection of nitrogen, compound 2(6mmol) and compound 3(1mmol) were added to 70mL of dry acetonitrile, and then dried potassium carbonate (18mmol) and potassium iodide (3mmol) were added, and the reaction was stirred under reflux for 8 hours. After the reaction is finished, the solvent is evaporated under reduced pressure, 60mL of dichloromethane is added, potassium carbonate is neutralized by 1M diluted hydrochloric acid until the pH value is 7, an organic layer is separated, the organic layer is concentrated, and a product is separated by 200-mesh silica gel column chromatography (an eluent is dichloromethane) to obtain a yellow solid, namely the fluorescent probe compound 1 (the molecular formula is C)73H56N4O12) Yield 83%.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent flow transformations made by using the contents of the present specification and the accompanying drawings, or applied directly or indirectly to other related technical fields, are included in the scope of the present invention.
Claims (7)
1. An AIE fluorescent probe for detecting deltamethrin, which is characterized in that the chemical name of the AIE fluorescent probe is (Z) -4- (1-cyano-2-styryl) -phenoxyacetic acid pentaerythrityl ester, and the molecular formula of the AIE fluorescent probe is C73H56N4O12The AIE fluorescent probe is a pentaerythritol tetraester structure with four cyanobenzene AIE structural units at the chain end, and the specific structure is as follows:
2. a preparation method of an AIE fluorescent probe for detecting deltamethrin is characterized in that the preparation method of the AIE fluorescent probe specifically comprises the following steps:
under the protection of nitrogen, mixing a compound 2 and a compound 3 in a molar ratio of 4-6: 1, adding into dry acetonitrile, adding dry potassium carbonate and potassium iodide, stirring, carrying out reflux reaction, after the reaction is finished, carrying out reduced pressure evaporation to remove a solvent, adding a proper amount of dichloromethane, neutralizing with dilute hydrochloric acid until the pH value is 7, separating an organic layer, concentrating, and separating a product through 200-mesh silica gel column chromatography to obtain a yellow solid compound 1, namely the AIE fluorescent probe (Z) -4- (1-cyano-2-styryl) -phenoxyacetic acid pentaerythritol ester; wherein: the compound 2 is hydroxyl cyano stilbene, and the compound 3 is chloracetic acid pentaerythritol ester.
3. The preparation method of the AIE fluorescent probe for detecting deltamethrin according to claim 2, characterized in that the molar ratio of the added potassium carbonate to the compound 2 is 1-3: 1.
4. The method for preparing an AIE fluorescent probe for detecting deltamethrin according to claim 2, wherein the molar ratio of the added potassium iodide to the compound 2 is 0.1-0.5: 1.
5. The preparation method of the AIE fluorescent probe for detecting deltamethrin according to claim 2, characterized in that the reaction time is 8-36 hours.
6. The method for preparing an AIE fluorescent probe for detecting deltamethrin according to claim 2, wherein the compound 2 hydroxycyano stilbene is prepared according to the published Master thesis of Fujian university.
7. The method for preparing an AIE fluorescent probe for detecting deltamethrin according to claim 2, wherein said compound 3 is pentaerythrityl chloroacetate prepared according to published literature "RSC Advances,2015,5(28): 21865-.
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| CN115894240A (en) * | 2022-10-14 | 2023-04-04 | 广州楷石医药有限公司 | Treprostinil prodrugs and uses thereof |
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| CN108997401A (en) * | 2018-08-30 | 2018-12-14 | 福建师范大学 | A kind of fluorescence probe and preparation method thereof for detecting lead ion |
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| CN108997401A (en) * | 2018-08-30 | 2018-12-14 | 福建师范大学 | A kind of fluorescence probe and preparation method thereof for detecting lead ion |
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| CN115894240A (en) * | 2022-10-14 | 2023-04-04 | 广州楷石医药有限公司 | Treprostinil prodrugs and uses thereof |
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