CN114920945B - Fluorescent probe based on amino-modified metal-organic framework material and detection method of benzaldehyde - Google Patents
Fluorescent probe based on amino-modified metal-organic framework material and detection method of benzaldehyde Download PDFInfo
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The invention discloses a fluorescent probe based on amino modified metal organic framework material, which is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, uniformly stirring, transferring into a polytetrafluoroethylene-lined reaction kettle, heating for hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning a product by using N, N-dimethylamide and ethanol, and finally centrifuging and drying to obtain the fluorescent probe. The invention also provides a benzaldehyde detection method. The fluorescent probe provided by the invention is easy to disperse in water, and can conveniently detect the benzaldehyde content in a water system; the minimum detection limit can reach 1 mu M, and the method has ultrahigh specific selectivity; the fluorescent probe provided by the invention has the advantages of simple and safe preparation process and low cost, and is suitable for large-scale production; the detection method of the benzaldehyde is simple to operate and high in practicability, and can realize rapid and sensitive detection of the benzaldehyde.
Description
Technical Field
The invention relates to the field of analytical chemistry, in particular to a fluorescent probe based on amino modified metal organic framework material and a detection method of benzaldehyde.
Background
Benzaldehyde is an important chemical raw material and has important application in the fields of plastics, lubricating oil, perfume, cosmetics and the like. However, studies have shown that benzaldehyde can elicit genotoxic and mutagenic effects. Excessive benzaldehyde in food can not only influence human health, but also cause serious harm to the environment. In addition, the content of benzaldehyde in the exhaled air of the gastric cancer patient is greatly different from that of the normal exhaled air of a human body, and the content of benzaldehyde in the exhaled air becomes an important tumor marker, so that the method has important application in tumor detection and treatment. Therefore, the method has important significance for rapid and sensitive detection of the benzaldehyde. Various analysis and spectroscopy methods are currently used for detecting benzaldehyde, but fluorescent probes applied to detecting benzaldehyde still deserve further development due to the advantages of high sensitivity, high selectivity, easy operability, short response time, low cost and the like. The benzaldehyde fluorescent probes used in China at present are almost all purchased from abroad, have high price and limited varieties, and have different defects. The metal organic framework nano material is a new crystal porous material, is formed by self-assembly of an organic bridging ligand serving as a support and metal serving as a node, has the characteristics of ultrahigh surface area, porous adjustability and easy modification, and has important application in the aspect of fluorescence detection. But now lacks a reliable solution.
Disclosure of Invention
The invention aims to solve the technical problem of providing a fluorescent probe based on amino modified metal organic framework material and a detection method of benzaldehyde aiming at the defects in the prior art. After amino groups are modified in the metal organic framework nano material, the detection of benzaldehyde can be carried out by utilizing the specific Schiff base condensation reaction between the amino groups and the benzaldehyde. The aniline has excellent fluorescence performance, and can form unique and stable condensation products with benzaldehyde to influence the fluorescence intensity of the aniline, so the invention designs a novel benzaldehyde detection fluorescent probe based on rare earth metal organic framework nano materials of 2-amino terephthalic acid ligand, and the concentration of the benzaldehyde can be detected.
In order to solve the technical problems, the invention adopts the following technical scheme: a fluorescent probe based on amino modified metal organic framework material is prepared by the following method:
dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, uniformly stirring, transferring into a polytetrafluoroethylene-lined reaction kettle, heating for hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning a product by using N, N-dimethylamide and ethanol, and finally centrifuging and drying to obtain the fluorescent probe.
Preferably, the fluorescent probe based on the amino modified metal organic framework material is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, uniformly stirring, transferring into a polytetrafluoroethylene-lined reaction kettle, heating to 80-150 ℃ for hydration heat synthesis reaction, reacting for 6-12 hours, cooling, sequentially cleaning a product by using the N, N-dimethylamide and ethanol, and finally centrifuging and drying to obtain the fluorescent probe.
Preferably, the fluorescent probe based on the amino modified metal organic framework material is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, stirring for 2 hours, transferring to a polytetrafluoroethylene-lined reaction kettle, heating to 150 ℃ for hydration heat synthesis reaction, reacting for 6 hours, cooling, washing a product with N, N-dimethylamide for 3 times, washing with ethanol for 3 times, and finally centrifugally drying to obtain the fluorescent probe.
Preferably, the volume ratio of N, N-dimethylamide to water in the mixed solvent is 6:1.
Preferably, the fluorescent probe based on the amino modified metal organic framework material is prepared by the following method: 1g of 2-amino terephthalic acid and 2g of terbium chloride hexahydrate are dissolved in a mixed solvent containing 60mL of N, N-dimethylamide and 10mL of water, the mixed solvent is stirred for 2 hours and then transferred into a reaction kettle with a polytetrafluoroethylene lining, the reaction kettle is heated to 150 ℃ for hydration heat synthesis reaction, the reaction is carried out for 6 hours, then the reaction kettle is cooled, the product is firstly washed 3 times with N, N-dimethylamide and then is washed 3 times with ethanol, and finally the fluorescent probe is obtained by centrifugal drying.
The invention also provides a detection method of benzaldehyde, which adopts the fluorescent probe based on the amino modified metal-organic framework material to detect benzaldehyde.
Preferably, the method comprises the steps of:
s1, constructing a standard curve for representing the relation between the concentration of benzaldehyde and fluorescence intensity;
s2, dispersing the fluorescent probe based on the amino modified metal organic framework material into water to prepare a detection solution;
s3, dissolving a sample of benzaldehyde to be detected in water to prepare a sample solution, mixing the detection solution obtained in the step S2 with the sample solution, uniformly stirring, standing, detecting the fluorescence intensity of a product at 460nm under 320nm excitation light, and finally calculating according to a standard curve to obtain the concentration of the benzaldehyde in the sample.
Preferably, the step S1 specifically includes: dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a standard detection solution, and uniformly dividing the standard detection solution into a plurality of parts; then adding benzaldehyde with different concentrations into each standard detection solution, uniformly stirring, and respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; and (3) performing curve fitting by taking the concentration of the benzaldehyde and the fluorescence intensity as the horizontal and vertical coordinates respectively to obtain a standard curve for representing the relation between the concentration of the benzaldehyde and the fluorescence intensity.
Preferably, the step S1 specifically includes:
dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a standard detection solution with the concentration of 0.2mg/mL, equally dividing into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of standard detection solution, and respectively adding benzaldehyde with the concentration of 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M into the 2 nd to 17 th parts of standard detection solutions in sequence; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; and (3) performing curve fitting by taking the concentration of the benzaldehyde and the fluorescence intensity as the horizontal and vertical coordinates respectively to obtain a standard curve for representing the relation between the concentration of the benzaldehyde and the fluorescence intensity.
Preferably, the method comprises the steps of:
s1, constructing a standard curve for representing the relation between the concentration of benzaldehyde and fluorescence intensity;
s2, dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a detection solution with the concentration of 0.2 mg/mL;
s3, dissolving a sample of benzaldehyde to be detected in water to prepare a sample solution, mixing 1mL of the detection solution obtained in the step S2 with 1mL of the sample solution, uniformly stirring, standing for 30 minutes, detecting the fluorescence intensity of a product at 460nm under 320nm of excitation light, and finally calculating according to a standard curve to obtain the concentration of the benzaldehyde in the sample.
The beneficial effects of the invention are as follows:
the fluorescent probe based on the amino-modified metal organic framework material provided by the invention is in a regular linear shape, has uniform size, has the length of about 1 mu m and the width of about 50nm, is easy to disperse in water, and can conveniently detect the benzaldehyde content in a water system; after benzaldehyde is added into the fluorescent probe, a fluorescent signal is reduced, the fluorescent signal is linearly related to the concentration of the benzaldehyde within the range of 0-100 mu M, and the minimum detection limit can reach 1 mu M; the fluorescent signal is not obviously reduced when other small organic molecules are added;
the fluorescent probe provided by the invention has the advantages of simple and safe preparation process and low cost, and is suitable for large-scale production;
the detection method of the benzaldehyde is simple to operate and high in practicability, and can realize rapid and sensitive detection of the benzaldehyde.
Drawings
FIG. 1 is a route for preparing a fluorescent probe based on an amino-modified metal-organic framework material prepared in example 1 of the present invention;
FIG. 2 is an SEM image of a fluorescent probe based on amino-modified metal-organic framework material prepared in example 1 of the present invention;
FIG. 3 is an excitation and emission spectrum of a fluorescent probe based on an amino-modified metal-organic framework material prepared in example 1 of the present invention;
FIG. 4 is a graph showing the change of fluorescence intensity with concentration of benzaldehyde for the fluorescent probe based on amino-modified metal-organic framework material prepared in example 1 of the present invention;
FIG. 5 is a linear relationship of fluorescence intensity of the fluorescent probe based on amino-modified metal-organic framework material prepared in example 1 according to the present invention as a function of benzaldehyde concentration;
FIG. 6 is a fluorescence spectrum of a fluorescent probe based on an amino-modified metal-organic framework material prepared in example 1 of the present invention when 200. Mu.M different kinds of small organic molecules are added;
FIG. 7 is a graph showing the comparison of fluorescence intensity values of the fluorescent probe based on the amino-modified metal-organic framework material prepared in example 1 of the present invention when 200. Mu.M different types of small organic molecules are added;
FIG. 8 is a schematic diagram of a mechanism analysis of detection of benzaldehyde by a fluorescent probe based on an amino-modified metal-organic framework material according to the present invention.
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Example 1
A fluorescent probe based on amino modified metal organic framework material is prepared by the following method:
1g of 2-amino terephthalic acid and 2g of terbium chloride hexahydrate are dissolved in a mixed solvent containing 60mL of N, N-dimethylamide and 10mL of water, the mixed solvent is vigorously stirred at normal temperature for 2 hours and then transferred into a polytetrafluoroethylene lining reaction kettle, the reaction kettle is placed into an oven, heated to 150 ℃ for hydration heat synthesis reaction, reacted for 6 hours, then cooled, and the product is firstly washed 3 times with N, N-dimethylamide, then washed 3 times with ethanol, and finally centrifugally dried, thus obtaining the fluorescent probe.
Referring to fig. 1 for a preparation route of the fluorescent probe based on the amino-modified metal-organic framework material, fig. 2 for an SEM electron microscope image thereof, it can be seen that the fluorescent probe is in a regular linear shape, has a uniform size, has a length of about 1 μm and a width of about 50 nm; FIG. 3 shows excitation and emission spectra, and it can be seen that the excitation peak is around 320nm and the emission is around 460 nm.
Referring to fig. 4, the change of fluorescence intensity of the fluorescent probe based on the amino-modified metal-organic framework material with the concentration of benzaldehyde is shown. In the example, firstly preparing 0.2mg/mL of rare earth metal organic framework nano material aqueous suspension, adding benzaldehyde (0, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M) with different concentrations into the suspension, uniformly stirring, and then respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; further, the concentration of benzaldehyde and the fluorescence intensity are respectively used as the horizontal and vertical coordinates to perform curve fitting, so as to obtain a standard curve for representing the relation between the concentration of benzaldehyde and the fluorescence intensity, as shown in fig. 5. It can be seen that the fluorescence intensity of the fluorescent probe is weakened along with the increase of the concentration of the benzaldehyde, and the fluorescent probe is in a linear relationship, so that the detection of the concentration of the benzaldehyde can be realized through the fluorescent probe based on the amino-modified metal-organic framework material.
Referring to FIG. 6, a fluorescence spectrum of the fluorescent probe based on the amino-modified metal-organic framework material when 200. Mu.M different types of small organic molecules are added, and FIG. 7 is a comparison result of fluorescence intensity values of the fluorescent probe when 200. Mu.M different types of small organic molecules are added. In this example, 0.2mg/mL of a fluorescent probe suspension based on an amino-modified metal-organic framework material was prepared, and then different small organic molecules (200. Mu.M) of the same solubility were added, and it can be seen that the fluorescence intensity was significantly reduced only when Benzaldehyde (Benzaldehyde) was added. Thus, it can be stated that the fluorescent probe can specifically detect benzaldehyde.
Referring to fig. 8, a schematic diagram of a mechanism analysis of detecting benzaldehyde by using the fluorescent probe based on amino modified metal organic framework material, wherein 2-amino terephthalic acid in the fluorescent probe is used as a supporting ligand of the metal organic framework material, and has strong fluorescence in water; the benzaldehyde can carry out specific Schiff base condensation reaction with amino groups on the 2-amino terephthalic acid, the generated Schiff base does not have fluorescence, the fluorescence intensity is reduced along with the increase of the addition amount of the benzaldehyde, other small organic molecules cannot carry out specific reaction with the 2-amino terephthalic acid, and the fluorescence performance of a fluorescent probe cannot be reduced, so that the fluorescent probe can specifically detect the benzaldehyde.
Example 2
A method for detecting benzaldehyde, the method comprising the steps of:
s1, constructing a standard curve for representing the relation between the concentration of benzaldehyde and fluorescence intensity;
dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a standard detection solution with the concentration of 0.2mg/mL, equally dividing into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of standard detection solution, and respectively adding benzaldehyde with the concentration of 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M into the 2 nd to 17 th parts of standard detection solutions in sequence; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; curve fitting was performed with the concentration of benzaldehyde and the fluorescence intensity as the horizontal and vertical coordinates, respectively, to obtain a standard curve representing the relationship between the concentration of benzaldehyde and the fluorescence intensity, as shown in fig. 5.
S2, dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a detection solution with the concentration of 0.2 mg/mL;
s3, dissolving a sample of benzaldehyde to be detected in water to prepare a sample solution, mixing 1mL of the detection solution obtained in the step S2 with 1mL of the sample solution, uniformly stirring, standing for 30 minutes, detecting the fluorescence intensity of a product at 460nm under 320nm of excitation light, and finally calculating according to a standard curve to obtain the concentration of the benzaldehyde in the sample.
Although embodiments of the present invention have been disclosed above, it is not limited to the use of the description and embodiments, it is well suited to various fields of use for the invention, and further modifications may be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the particular details without departing from the general concepts defined in the claims and the equivalents thereof.
Claims (9)
1. A detection method of benzaldehyde is characterized in that the method adopts a fluorescent probe based on amino modified metal organic framework material to detect benzaldehyde;
the fluorescent probe based on the amino modified metal organic framework material is prepared by the following method:
dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, uniformly stirring, transferring into a polytetrafluoroethylene-lined reaction kettle, heating for hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning a product by using N, N-dimethylamide and ethanol, and finally centrifuging and drying to obtain the fluorescent probe.
2. The detection method of benzaldehyde according to claim 1, wherein the fluorescent probe based on amino modified metal organic framework material is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, uniformly stirring, transferring into a polytetrafluoroethylene-lined reaction kettle, heating to 80-150 ℃ for hydration heat synthesis reaction, reacting for 6-12 hours, cooling, sequentially cleaning a product by using the N, N-dimethylamide and ethanol, and finally centrifuging and drying to obtain the fluorescent probe.
3. The detection method of benzaldehyde according to claim 2, wherein the fluorescent probe based on amino modified metal organic framework material is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethylamide and water, stirring for 2 hours, transferring to a polytetrafluoroethylene-lined reaction kettle, heating to 150 ℃ for hydration heat synthesis reaction, reacting for 6 hours, cooling, washing a product with N, N-dimethylamide for 3 times, washing with ethanol for 3 times, and finally centrifugally drying to obtain the fluorescent probe.
4. The method for detecting benzaldehyde according to claim 3, wherein the volume ratio of N, N-dimethylamide to water in the mixed solvent is 6:1.
5. The method for detecting benzaldehyde according to claim 4, which is prepared by the following steps: 1g of 2-amino terephthalic acid and 2g of terbium chloride hexahydrate are dissolved in a mixed solvent containing 60mL of N, N-dimethylamide and 10mL of water, the mixed solvent is stirred for 2 hours and then transferred into a reaction kettle with a polytetrafluoroethylene lining, the reaction kettle is heated to 150 ℃ for hydration heat synthesis reaction, the reaction is carried out for 6 hours, then the reaction kettle is cooled, the product is firstly washed 3 times with N, N-dimethylamide and then is washed 3 times with ethanol, and finally the fluorescent probe is obtained by centrifugal drying.
6. The method for detecting benzaldehyde according to claim 1, which comprises the steps of:
s1, constructing a standard curve for representing the relation between the concentration of benzaldehyde and fluorescence intensity;
s2, dispersing the fluorescent probe based on the amino modified metal organic framework material into water to prepare a detection solution;
s3, dissolving a sample of benzaldehyde to be detected in water to prepare a sample solution, mixing the detection solution obtained in the step S2 with the sample solution, uniformly stirring, standing, detecting the fluorescence intensity of a product at 460nm under 320nm excitation light, and finally calculating according to a standard curve to obtain the concentration of the benzaldehyde in the sample.
7. The method for detecting benzaldehyde according to claim 6, wherein the step S1 specifically comprises: dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a standard detection solution, and uniformly dividing the standard detection solution into a plurality of parts; then adding benzaldehyde with different concentrations into each standard detection solution, uniformly stirring, and respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; and (3) performing curve fitting by taking the concentration of the benzaldehyde and the fluorescence intensity as the horizontal and vertical coordinates respectively to obtain a standard curve for representing the relation between the concentration of the benzaldehyde and the fluorescence intensity.
8. The method for detecting benzaldehyde according to claim 7, wherein the step S1 is specifically:
dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a standard detection solution with the concentration of 0.2mg/mL, equally dividing into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of standard detection solution, and respectively adding benzaldehyde with the concentration of 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M into the 2 nd to 17 th parts of standard detection solutions in sequence; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under 320nm of excitation light; and (3) performing curve fitting by taking the concentration of the benzaldehyde and the fluorescence intensity as the horizontal and vertical coordinates respectively to obtain a standard curve for representing the relation between the concentration of the benzaldehyde and the fluorescence intensity.
9. The method for detecting benzaldehyde according to claim 8, which comprises the steps of:
s1, constructing a standard curve for representing the relation between the concentration of benzaldehyde and fluorescence intensity;
s2, dispersing the fluorescent probe based on the amino modified metal organic framework material in water to prepare a detection solution with the concentration of 0.2 mg/mL;
s3, dissolving a sample of benzaldehyde to be detected in water to prepare a sample solution, mixing 1mL of the detection solution obtained in the step S2 with 1mL of the sample solution, uniformly stirring, standing for 30 minutes, detecting the fluorescence intensity of a product at 460nm under 320nm of excitation light, and finally calculating according to a standard curve to obtain the concentration of the benzaldehyde in the sample.
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