CN114920945A - Fluorescence probe based on amino modified metal organic framework material and detection method of benzaldehyde - Google Patents
Fluorescence probe based on amino modified metal organic framework material and detection method of benzaldehyde Download PDFInfo
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Abstract
The invention discloses a fluorescent probe based on an 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-dimethyl amide and water, uniformly stirring, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to perform a hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning a product by using N, N-dimethyl amide and ethanol, and finally centrifugally 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 be used for conveniently detecting the content of benzaldehyde in a water system; the lowest detection limit can reach 1 mu M, and the specific selectivity is ultrahigh; the fluorescent probe provided by the invention has simple and safe preparation process and low cost, and is suitable for large-scale production; the method for detecting the benzaldehyde is simple to operate and high in practicability, and can realize quick and sensitive detection of the benzaldehyde.
Description
Technical Field
The invention relates to the field of analytical chemistry, in particular to a fluorescence probe based on an 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, spices, cosmetics and the like. However, it has been shown that benzaldehyde can trigger genotoxic and mutagenic effects. Excessive benzaldehyde in food can not only affect human health, but also cause serious harm to the environment. In addition, the content of benzaldehyde in the exhaled air of a gastric cancer patient is greatly different from that of 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 rapid and sensitive detection of the benzaldehyde is of great significance. At present, various analysis and spectroscopy methods are used for detecting benzaldehyde, but the fluorescent probe applied to detecting benzaldehyde is still worthy of further development due to the advantages of high sensitivity, high selectivity, easiness in operation, short response time, low cost and the like. At present, the benzaldehyde fluorescent probes used in China are almost all purchased from foreign countries, are high in price and limited in variety, and have different defects. The metal organic framework nano material is a new emerging crystal porous material, is formed by self-assembling an organic bridging ligand serving as a strut and metal serving as a node, has the characteristics of ultrahigh surface area, adjustability of porosity and easiness in modification, and has important application in the aspect of fluorescence detection. But now a reliable solution is lacking.
Disclosure of Invention
The technical problem to be solved by the present invention is to provide a fluorescent probe based on an amino-modified metal-organic framework material and a detection method of benzaldehyde, aiming at the defects in the prior art. After amino is modified in the metal organic framework nano material, the benzaldehyde can be detected by utilizing the specific Schiff base condensation reaction between the amino and the benzaldehyde. The aniline has excellent fluorescence performance, and can form a unique and stable condensation product with benzaldehyde to influence the fluorescence intensity of the aniline, so that the invention designs a novel benzaldehyde detection fluorescent probe of a rare earth metal organic framework nano material based on a 2-amino terephthalic acid ligand, and the benzaldehyde concentration can be detected.
In order to solve the technical problems, the invention adopts the technical scheme that: a fluorescent probe based on an amino modified metal organic framework material is prepared by the following steps:
dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethyl amide and water, uniformly stirring, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating for hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning products by using N, N-dimethyl amide and ethanol, and finally centrifugally 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-dimethyl amide and water, uniformly stirring, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 80-150 ℃ to perform a hydration thermal synthesis reaction for 6-12 hours, cooling, sequentially cleaning a product by using N, N-dimethyl amide and ethanol, and finally performing centrifugal 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-dimethyl amide and water, stirring for 2 hours, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 150 ℃ to perform a hydration thermal synthesis reaction, reacting for 6 hours, cooling, washing a product for 3 times by using N, N-dimethyl amide, washing for 3 times by using ethanol, and finally centrifugally drying to obtain the fluorescent probe.
Preferably, the volume ratio of the 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: dissolving 1g of 2-aminoterephthalic acid and 2g of terbium trichloride hexahydrate in a mixed solvent containing 60mL of N, N-dimethyl amide and 10mL of water, stirring for 2 hours, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 150 ℃ to perform a hydration thermal synthesis reaction for 6 hours, cooling, washing a product with N, N-dimethyl amide for 3 times, then washing with ethanol for 3 times, and finally performing centrifugal drying to obtain the fluorescent probe.
The invention also provides a method for detecting 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 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;
s3, dissolving the sample to be detected with benzaldehyde in water to prepare a sample solution, then mixing the detection solution obtained in the step S2 with the sample solution, stirring uniformly, standing, detecting the fluorescence intensity of the product at 460nm under the excitation light of 320nm, and finally calculating according to a standard curve to obtain the concentration of benzaldehyde in the sample.
Preferably, step S1 is specifically: dispersing the fluorescent probes based on the amino modified metal organic framework material in water to prepare a standard detection solution, and uniformly dividing into a plurality of parts; adding benzaldehyde with different concentrations into each standard detection solution, stirring uniformly, and respectively detecting the fluorescence intensity of the product at 460nm under excitation light of 320 nm; and respectively taking the concentration and the fluorescence intensity of the benzaldehyde as a horizontal coordinate and a vertical coordinate, and performing curve fitting to obtain a standard curve representing the relation between the concentration and the fluorescence intensity of the benzaldehyde.
Preferably, 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, dividing the standard detection solution into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of the standard detection solution, and respectively adding benzaldehyde with the volume of V into the 2 nd to 17 th parts of the standard detection solution, wherein the benzaldehyde with the concentration of V is sequentially 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 MuM; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under the excitation light of 320 nm; and (3) respectively taking the concentration of the benzaldehyde and the fluorescence intensity as a horizontal coordinate and a vertical coordinate, and performing curve fitting to obtain a standard curve 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 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 to be detected for benzaldehyde into water to prepare a sample solution, then mixing 1mL of the detection solution obtained in the step S2 with 1mL of the sample solution, stirring uniformly, standing for 30 minutes, detecting the fluorescence intensity of a product at 460nm under excitation light of 320nm, and finally calculating according to a standard curve to obtain the concentration of benzaldehyde in the sample.
The invention has the beneficial effects that:
the fluorescent probe based on the amino modified metal organic framework material is regular and linear, has uniform size, length of about 1 mu m and width of about 50nm, is easy to disperse in water, and can conveniently detect the content of benzaldehyde in a water system; after benzaldehyde is added into the fluorescent probe, the 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 lowest detection limit can reach 1 mu M; the chiral nematic liquid has ultrahigh specific selectivity to benzaldehyde, and a fluorescence signal cannot be obviously reduced when other organic micromolecules are added;
the fluorescent probe provided by the invention has simple and safe preparation process and low cost, and is suitable for large-scale production;
the method for detecting the benzaldehyde is simple to operate and high in practicability, and can realize quick and sensitive detection of the benzaldehyde.
Drawings
FIG. 1 is a preparation route of 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 electron micrograph of the fluorescent probe based on the amino-modified metal-organic framework material prepared in example 1 of the 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 shows the variation of fluorescence intensity with benzaldehyde concentration of the fluorescent probe based on the 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 the amino-modified metal-organic framework material prepared in example 1 of the present invention with the change of benzaldehyde concentration;
FIG. 6 is a fluorescence spectrum of the amino-modified metal-organic framework material-based fluorescent probe prepared in example 1 of the present invention when 200. mu.M of different types of small organic molecules are added;
FIG. 7 is a comparison result 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 of different types of small organic molecules are added;
FIG. 8 is a schematic diagram of the mechanism analysis of benzaldehyde detection by the amino-modified metal-organic framework material-based fluorescent probe of the present invention.
Detailed Description
The present invention is further described in detail below with reference to examples so that those skilled in the art can practice the invention with reference 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 combinations thereof. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are conventional products which are not indicated by manufacturers and are commercially available.
Example 1
A fluorescent probe based on an amino modified metal organic framework material is prepared by the following method:
1g of 2-aminoterephthalic acid and 2g of terbium trichloride hexahydrate are dissolved in a mixed solvent containing 60mL of N, N-dimethyl amide and 10mL of water, are stirred vigorously at normal temperature for 2 hours and then are transferred to a reaction kettle with a polytetrafluoroethylene lining, the reaction kettle is placed in an oven, is heated to 150 ℃ for a hydration thermal synthesis reaction for 6 hours, is cooled, and is cleaned by N, N-dimethyl amide for 3 times, then is cleaned by ethanol for 3 times, and finally is centrifugally dried to obtain the fluorescent probe.
Referring to fig. 1, a preparation route of the fluorescent probe based on the amino-modified metal-organic framework material is shown, and fig. 2 is an SEM (electron microscope) image of the fluorescent probe, which shows that the fluorescent probe is regular and linear, has uniform size, is about 1 μm long, and is about 50nm wide; FIG. 3 is the 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 fluorescence intensity of the fluorescent probe based on the amino-modified metal-organic framework material is shown as a function of the concentration of benzaldehyde. In this example, 0.2mg/mL aqueous suspension of the rare earth metal organic framework nanomaterial is prepared, benzaldehyde (0, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400, 500 μ M) with different concentrations is added into the suspension, and after uniform stirring, the fluorescence intensity of the product at 460nm under excitation light of 320nm is respectively detected; further, the concentration of benzaldehyde and the fluorescence intensity are respectively taken as a horizontal coordinate and a vertical coordinate, curve fitting is carried out, and a standard curve representing the relation between the concentration of benzaldehyde and the fluorescence intensity is obtained, as shown in fig. 5. As can be seen, 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 relation, 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, it is a fluorescence spectrum of the fluorescent probe based on the amino-modified metal-organic framework material when 200 μ M of 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 μ M of 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. Therefore, it can be shown that the fluorescent probe can specifically detect benzaldehyde.
Referring to fig. 8, which is a schematic diagram of a mechanism analysis of detecting benzaldehyde by the fluorescent probe based on the amino-modified metal-organic framework material, 2-aminoterephthalic acid in the fluorescent probe is used as a supporting ligand of the metal-organic framework material, and has strong fluorescence in water; benzaldehyde can be subjected to a specific Schiff base condensation reaction with amino on 2-aminoterephthalic acid, the generated Schiff base does not have fluorescence, the fluorescence intensity is reduced along with the increase of the addition of benzaldehyde, other small organic molecules cannot be subjected to a specific reaction with 2-aminoterephthalic acid, and the fluorescence performance of a fluorescence probe cannot be reduced, so that the fluorescence probe can be used for specifically detecting benzaldehyde.
Example 2
A method for detecting benzaldehyde comprises the following steps:
s1, constructing a standard curve 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, dividing the standard detection solution into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of the standard detection solution, and respectively adding benzaldehyde with the volume of V, the concentration of which is 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M into the standard detection solutions from the 2 nd part to the 17 th part; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under the excitation light of 320 nm; taking the concentration of benzaldehyde and fluorescence intensity as horizontal and vertical coordinates respectively, performing curve fitting to obtain a standard curve representing the relationship between the concentration of benzaldehyde and 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 to be detected for benzaldehyde into 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 excitation light of 320nm, and finally calculating according to a standard curve to obtain the concentration of benzaldehyde in the sample.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the details shown in the description and the examples, which are set forth, but are fully applicable to various fields of endeavor as are suited to the particular use contemplated, and further modifications will readily occur to those skilled in the art, since the invention is not limited to the details shown and described without departing from the general concept as defined by the appended claims and their equivalents.
Claims (10)
1. A fluorescent probe based on an amino modified metal organic framework material is characterized by being prepared by the following method:
dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethyl amide and water, uniformly stirring, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating for hydration thermal synthesis reaction, cooling after the reaction is finished, sequentially cleaning products by using N, N-dimethyl amide and ethanol, and finally centrifugally drying to obtain the fluorescent probe.
2. The fluorescent probe based on the amino modified metal organic framework material of claim 1, which is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethyl amide and water, uniformly stirring, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 80-150 ℃ to perform a hydration thermal synthesis reaction for 6-12 hours, cooling, sequentially cleaning a product by using N, N-dimethyl amide and ethanol, and finally centrifugally drying to obtain the fluorescent probe.
3. The fluorescent probe based on the amino modified metal organic framework material of claim 2, which is prepared by the following method: dissolving 2-amino terephthalic acid and terbium trichloride hexahydrate in a mixed solvent of N, N-dimethyl amide and water, stirring for 2 hours, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 150 ℃ to perform a hydration thermal synthesis reaction, reacting for 6 hours, cooling, washing a product for 3 times by using N, N-dimethyl amide, washing for 3 times by using ethanol, and finally centrifugally drying to obtain the fluorescent probe.
4. The fluorescence probe based on the amino-modified metal-organic framework material of claim 3, wherein the volume ratio of N, N-dimethyl amide to water in the mixed solvent is 6: 1.
5. The fluorescent probe based on the amino modified metal organic framework material of claim 4, which is prepared by the following method: dissolving 1g of 2-aminoterephthalic acid and 2g of terbium trichloride hexahydrate in a mixed solvent containing 60mL of N, N-dimethyl amide and 10mL of water, stirring for 2 hours, transferring to a reaction kettle with a polytetrafluoroethylene lining, heating to 150 ℃ to perform a hydration thermal synthesis reaction for 6 hours, cooling, washing a product with N, N-dimethyl amide for 3 times, then washing with ethanol for 3 times, and finally performing centrifugal drying to obtain the fluorescent probe.
6. A method for detecting benzaldehyde, which is characterized in that the method adopts the fluorescent probe based on the amino modified metal organic framework material as claimed in any one of claims 1 to 5 to detect benzaldehyde.
7. The method for detecting benzaldehyde according to claim 6, wherein the method comprises the steps of:
s1, constructing a standard curve 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;
s3, dissolving the sample to be detected with benzaldehyde in water to prepare a sample solution, then mixing the detection solution obtained in the step S2 with the sample solution, stirring uniformly, standing, detecting the fluorescence intensity of the product at 460nm under the excitation light of 320nm, and finally calculating according to a standard curve to obtain the concentration of benzaldehyde in the sample.
8. The benzaldehyde detection method according to claim 7, wherein the step S1 specifically comprises: dispersing the fluorescent probes based on the amino modified metal organic framework material in water to prepare a standard detection solution, and uniformly dividing into a plurality of parts; adding benzaldehyde with different concentrations into each standard detection solution, stirring uniformly, and respectively detecting the fluorescence intensity of the product at 460nm under excitation light of 320 nm; and respectively taking the concentration and the fluorescence intensity of the benzaldehyde as a horizontal coordinate and a vertical coordinate, and performing curve fitting to obtain a standard curve representing the relation between the concentration and the fluorescence intensity of the benzaldehyde.
9. The method for detecting benzaldehyde according to claim 8, wherein 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, dividing the standard detection solution into 17 parts with the volume of V, adding deionized water with the volume of V into the 1 st part of the standard detection solution, and respectively adding benzaldehyde with the volume of V, the concentration of which is 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400 and 500 mu M into the standard detection solutions from the 2 nd part to the 17 th part; stirring uniformly, standing for 30 minutes, and respectively detecting the fluorescence intensity of the product at 460nm under the excitation light of 320 nm; and respectively taking the concentration and the fluorescence intensity of the benzaldehyde as a horizontal coordinate and a vertical coordinate, and performing curve fitting to obtain a standard curve representing the relation between the concentration and the fluorescence intensity of the benzaldehyde.
10. The method for detecting benzaldehyde according to claim 9, wherein the method comprises the steps of:
s1, constructing a standard curve 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 to be detected for benzaldehyde into 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 excitation light of 320nm, and finally calculating according to a standard curve to obtain the concentration of benzaldehyde in the sample.
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| CN106188110A (en) * | 2016-07-13 | 2016-12-07 | 北京化工大学 | A kind of metallic organic framework functional fluorescence material and preparation method and applications |
| CN111363161A (en) * | 2020-04-21 | 2020-07-03 | 周口师范学院 | Thorium ion fluorescent probe based on terbium-organic framework material and preparation method thereof |
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| CN101678266A (en) * | 2007-04-05 | 2010-03-24 | 巴斯夫欧洲公司 | Mixture containing an organometallic skeletal material, and PCM device |
| US20100126344A1 (en) * | 2007-04-05 | 2010-05-27 | Basf Se | Mixture comprising a metal organic framework and also a latent heat store |
| CN105753891A (en) * | 2016-03-23 | 2016-07-13 | 浙江大学 | Rare earth organic framework material for fluorescence detection of trace water and preparation method of rare earth organic framework material |
| CN106188110A (en) * | 2016-07-13 | 2016-12-07 | 北京化工大学 | A kind of metallic organic framework functional fluorescence material and preparation method and applications |
| CN111363161A (en) * | 2020-04-21 | 2020-07-03 | 周口师范学院 | Thorium ion fluorescent probe based on terbium-organic framework material and preparation method thereof |
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