CN116496461A - Covalent organic framework material and preparation method and application thereof - Google Patents
Covalent organic framework material and preparation method and application thereof Download PDFInfo
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- CN116496461A CN116496461A CN202310502393.5A CN202310502393A CN116496461A CN 116496461 A CN116496461 A CN 116496461A CN 202310502393 A CN202310502393 A CN 202310502393A CN 116496461 A CN116496461 A CN 116496461A
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- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims abstract description 32
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/3103—Atomic absorption analysis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Plasma & Fusion (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The application relates to the technical field of chemical analysis, in particular to a covalent organic framework material and a preparation method and application thereof. The chemical components of the covalent organic framework material comprise: terephthalaldehyde and 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin; wherein the weight ratio of terephthalaldehyde to 5,10,15, 20-tetra (4-aminophenyl) porphyrin is 2-4: 5. the application solves the technical problem that the stability of the existing covalent organic framework material in analysis and detection is poor.
Description
Technical Field
The application relates to the technical field of chemical analysis, in particular to a covalent organic framework material and a preparation method and application thereof.
Background
Covalent organic framework compounds (Covalent organic frameworks, COFs) are crystalline organic polymers with porous structures constructed from light elements such as C, H, B, O, N through covalent bonds. The covalent organic framework compound is used as nano enzyme, has better oxide mimic enzyme activity, but unstable hydrogen peroxide needs to be added in the process of detecting ascorbic acid (vitamin C, vc), so that the cost is increased, and the stability of a detection result is reduced.
Disclosure of Invention
The application provides a covalent organic framework material, a preparation method and application thereof, and aims to solve the technical problem that the existing covalent organic framework material is poor in stability in analysis and detection.
In a first aspect, the present application provides a covalent organic framework material having a chemical composition comprising:
terephthalaldehyde and 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin; wherein, the liquid crystal display device comprises a liquid crystal display device,
the weight ratio of the terephthalaldehyde to the 5,10,15, 20-tetra (4-aminophenyl) porphyrin is 2-4: 5.
optionally, the weight ratio of terephthalaldehyde to 5,10,15, 20-tetra (4-aminophenyl) porphyrin is 3:5.
in a second aspect, the present application provides the use of a covalent organic framework material according to any one of the embodiments of the first aspect for the detection of ascorbic acid.
In a third aspect, the present application provides a method for preparing a covalent organic framework material according to any one of the embodiments of the first aspect, the method comprising:
mixing terephthalaldehyde, 5,10,15, 20-tetra (4-aminophenyl) porphyrin and a solvent, and heating under the condition of a set temperature to obtain a reaction solution;
and centrifuging and drying the reaction liquid to obtain the covalent organic framework material.
Optionally, the set temperature is 50-150 ℃.
Optionally, the set temperature is 90 ℃.
Optionally, the heating time is 24-72 h.
Optionally, the heating time is 48 hours.
Optionally, the solvent is dimethyl sulfoxide, and the volume V of the dimethyl sulfoxide and the weight M of the terephthalaldehyde satisfy the relationship: v: m=1 to 3:1.
optionally, the volume V of the dimethyl sulfoxide and the weight M of the terephthalaldehyde satisfy the relationship: v: m=1: 1.
compared with the prior art, the technical scheme provided by the embodiment of the application has the following advantages:
the covalent organic framework material (COFs) provided by the embodiment of the application has oxidase catalysis property, can effectively prevent and control porphyrin aggregation, and the porous structure of the COFs is beneficial to substrate aggregation, enhances electron transfer and enhances the catalytic activity of enzyme; the COFs mimic enzyme can directly catalyze TMB reaction, hydrogen peroxide is not needed, the operation is simpler and more convenient, the stability and the accuracy of a reaction system are improved, the cost is reduced, and the pollution to the environment is reduced; the mimic enzyme can be used for detecting ascorbic acid at room temperature, is simple, convenient and quick, has high sensitivity, and has very strong practical application prospect.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings that are required to be used in the description of the embodiments or the prior art will be briefly described below, and it will be obvious to those skilled in the art that other drawings can be obtained from these drawings without inventive effort.
FIG. 1 is a synthetic scheme of a COFS mimic enzyme provided in the examples of the present application;
FIG. 2 is an SEM and TEM image of a COFs mimetic enzyme provided in the examples of the present application;
FIG. 3 is an XRD pattern of a COFs mimetic enzyme provided in the examples of the present application;
FIG. 4 is an infrared spectrum of a COFs mimic enzyme provided in an embodiment of the present application;
FIG. 5 is an XPS diagram of a COFS mimetic enzyme provided in the examples herein;
FIG. 6 is a 13C nuclear magnetic resonance diagram of a COFs mimetic enzyme provided in the examples of the present application;
FIG. 7 is a graph showing the catalytic activity of a COFs mimetic enzyme provided in the examples of the present application;
FIG. 8 is a diagram showing the enzyme kinetics of a COFs mimetic enzyme provided in the examples of the present application;
FIG. 9 is a graph showing the response of the detection platform to ascorbic acid during different reaction times provided in the examples of the present application;
FIG. 10 is a graph showing the response of the detection platform to ascorbic acid at different pH values provided in the examples of the present application;
FIG. 11 is a graph showing the response of the different reaction temperature detection platforms provided in the examples of the present application to ascorbic acid;
FIG. 12 is a graph showing the detection results and linear calibration curves of COFS mimic enzyme for different concentrations of ascorbic acid according to the examples of the present application;
FIG. 13 shows the results of specific detection of ascorbic acid by a COFS mimic enzyme provided in the examples herein;
FIG. 14 is a graph showing the catalytic performance of COFs prepared under various synthesis conditions provided in the examples of the present application;
fig. 15 is a preparation method of COFs provided in the embodiment of the present application.
Detailed Description
For the purposes of making the objects, technical solutions and advantages of the embodiments of the present application more clear, the technical solutions of the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is apparent that the described embodiments are some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by one of ordinary skill in the art without undue burden from the present disclosure, are within the scope of the present application based on the embodiments herein.
Various embodiments of the present application may exist in a range format; it should be understood that the description in a range format is merely for convenience and brevity and should not be interpreted as a rigid limitation on the scope of the application. It is therefore to be understood that the range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that a description of a range from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, wherever applicable. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
In this application, unless otherwise indicated, terms of orientation such as "upper" and "lower" are used specifically to refer to the orientation of the drawing in the figures. In addition, in the description of the present application, the terms "include", "comprise", "comprising" and the like mean "including but not limited to". Relational terms such as "first" and "second", and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Herein, "and/or" describing an association relationship of an association object means that there may be three relationships, for example, a and/or B, may mean: a alone, a and B together, and B alone. Wherein A, B may be singular or plural. Herein, "at least one" means one or more, and "a plurality" means two or more. "at least one", "at least one" or the like refer to any combination of these items, including any combination of single item(s) or plural items(s). For example, "at least one (individual) of a, b, or c," or "at least one (individual) of a, b, and c," may each represent: a, b, c, a-b (i.e., a and b), a-c, b-c, or a-b-c, wherein a, b, c may be single or multiple, respectively.
Unless specifically indicated otherwise, the various raw materials, reagents, instruments, equipment, and the like used in this application are commercially available or may be prepared by existing methods.
In a first aspect, the present application provides a covalent organic framework material having a chemical composition comprising:
terephthalaldehyde and 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin; wherein, the liquid crystal display device comprises a liquid crystal display device,
the weight ratio of the terephthalaldehyde to the 5,10,15, 20-tetra (4-aminophenyl) porphyrin is 2-4: 5.
in some embodiments, the weight ratio of terephthalaldehyde to 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin is 3:5.
in the covalent organic framework material, the effect of terephthalaldehyde: linking of the framework of the covalent organic framework material. Action of 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin: the covalent backbone material is the primary source of catalytic function.
Controlling the weight ratio of terephthalaldehyde to 5,10,15, 20-tetra (4-aminophenyl) porphyrin to be 2-4: 5 positive effects: catalytic function of the product. If the content of terephthalaldehyde is too high or the content of 5,10,15, 20-tetra (4-aminophenyl) porphyrin is too low, the catalytic performance of the product can be reduced to a certain extent; if the content of terephthalaldehyde is too low or the content of 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin is too high, the yield of the product may be lowered to some extent. Specifically, the weight ratio of terephthalaldehyde to 5,10,15, 20-tetra (4-aminophenyl) porphyrin may be 2: 5. 3:5. 4:5, etc., preferably, the weight ratio is 3:5.
in a second aspect, the present application provides the use of a covalent organic framework material according to any one of the embodiments of the first aspect for the detection of ascorbic acid.
Ascorbic acid (vitamin C, vc) is a water-soluble vitamin essential to the human body and is widely found in fresh fruits and vegetables. Because of its good antioxidant activity, ascorbic acid can maintain immune system function, prevent gingival bleeding, etc. Because the human body cannot synthesize the ascorbic acid, the ascorbic acid can only be taken in through the outside. Both overintake and lack of intake can lead to certain diseases. Currently, vegetables and fruits are the main sources of ascorbic acid intake by humans. In addition, ascorbic acid is widely used as a natural antioxidant in the fields of medical pharmacy, food processing, cosmetics, and the like. Therefore, it is important to analyze the ascorbic acid content of foods and pharmaceuticals by a highly sensitive, simple method. The current detection methods of Vc include titration, chromatography, capillary electrophoresis, electrophoresis and fluorescence. Among the detection methods, the colorimetric method judges the content of the object to be detected through the change of the color of the reaction system, and has the unique advantages of simplicity, convenience, rapidness, visibility to naked eyes, low cost and the like. However, the enzyme required by the colorimetric method has the problems of poor stability and severe storage conditions, and affects the stability of detection. To increase the stability of the assay, it is desirable to increase the stability of the enzyme during the colorimetric process.
The covalent organic framework materials (COFs) of the first aspect have oxidase catalysis properties, and the mimic enzyme can be used for detecting ascorbic acid at room temperature, is simple, convenient and quick, has high sensitivity and has very strong practical application prospect.
In a third aspect, the present application provides a method for preparing a covalent organic framework material, please refer to fig. 15, for preparing a covalent organic framework material according to any one of the embodiments of the first aspect, the method comprising:
s1, mixing terephthalaldehyde, 5,10,15, 20-tetra (4-aminophenyl) porphyrin and a solvent, and heating under the condition of a set temperature to obtain a reaction solution;
s2, centrifuging and drying the reaction liquid to obtain the covalent organic framework material.
In some embodiments, the set temperature is 50 to 150 ℃.
In some embodiments, the set temperature is 90 ℃.
"set temperature" means the temperature of the heating, and the positive effect of controlling the temperature of the heating to 50 to 150 ℃ is that: meets the requirements of production, cost, environmental protection and the like. If the temperature is too high, the content of byproducts is increased to a certain extent; if the temperature is too low, the synthesis efficiency is lowered to some extent. Specifically, the temperature may be 50 ℃,100 ℃,150 ℃, etc., and preferably, the temperature may be 90 ℃.
In some embodiments, the heating is for a period of 24 to 72 hours.
In some embodiments, the heating time is 48 hours.
The positive effect of controlling the heating time to be 24-72 h is that: meeting the requirements of cost and product yield. If the time is too long, the time cost and the content of byproducts are increased to a certain extent; if the time is too short, the synthesis yield is somewhat reduced. Specifically, the heating time may be 24h, 30h, 40h, 50h, 60h, 72h, etc., and preferably the heating time is 48h.
In some embodiments, the solvent is dimethyl sulfoxide, the volume V of which satisfies the relationship with the weight M of terephthalaldehyde: v: m=1 to 3:1.
in some embodiments, the volume V of the dimethyl sulfoxide and the weight M of the terephthalaldehyde satisfy the relationship: v: m=1: 1.
the dimethyl sulfoxide is selected as the positive effect of the solvent: optimal reaction rates and product yields are obtained.
Controlling the ratio of the volume of dimethyl sulfoxide to the weight of terephthalaldehyde to be 1-3: 1 positive effects: the reaction rate and the product yield are ensured. If the volume of dimethyl sulfoxide is too large or the weight of terephthalaldehyde is too small, the reaction rate can be influenced to a certain extent; if the volume of dimethyl sulfoxide is too small or the weight of terephthalaldehyde is too large, the product yield may be affected to some extent. Specifically, the ratio may be 1:1. 2: 1. 3:1, etc., preferably, the ratio is 1:1.
the preparation method of the covalent organic framework material is realized based on the covalent organic framework material, and specific chemical components of the covalent organic framework material can refer to the embodiment, and because the preparation method of the covalent organic framework material adopts part or all of the technical schemes of the embodiment, the preparation method at least has all the beneficial effects brought by the technical schemes of the embodiment, and the description is omitted herein.
The present application is further illustrated below in conjunction with specific examples. It should be understood that these examples are illustrative only of the present application and are not intended to limit the scope of the present application. The experimental procedures, which are not specified in the following examples, are generally determined according to national standards. If the corresponding national standard does not exist, the method is carried out according to the general international standard, the conventional condition or the condition recommended by the manufacturer.
Preparation of COFs:
s1, mixing terephthalaldehyde, 5,10,15, 20-tetra (4-aminophenyl) porphyrin and dimethyl sulfoxide solution, and heating under the condition of a set temperature to obtain a reaction solution;
s2, centrifuging and drying the reaction liquid to obtain the covalent organic framework material.
TABLE 1 composition of covalent organic framework materials
Example 1
6mg of terephthalaldehyde was weighed and dissolved in 6mL of dimethyl sulfoxide solution, 10mg of 5,10,15, 20-tetra (4-aminophenyl) porphyrin was added, and after mixing, the mixture was reacted at 90℃for 48 hours. Centrifuging at 8000rpm/min for 5min, washing the collected solid with tetrahydrofuran and ethanol for 3 times, and drying the white solid in a vacuum oven at 65 ℃ overnight to obtain the solid which is the COFs1 material.
Example 2
4mg of terephthalaldehyde was weighed and dissolved in 8mL of dimethyl sulfoxide solution, 10mg of 5,10,15, 20-tetra (4-aminophenyl) porphyrin was added, and after mixing, the mixture was reacted at 50℃for 40 hours. Centrifuging at 8000rpm/min for 5min, washing the collected solid with tetrahydrofuran and ethanol for 3 times, and drying the white solid in a vacuum oven at 60 ℃ overnight to obtain a solid which is the COFs2 material.
Example 3
8mg of terephthalaldehyde was weighed and dissolved in 24mL of dimethyl sulfoxide solution, 10mg of 5,10,15, 20-tetra (4-aminophenyl) porphyrin was added, and after mixing, the mixture was reacted at 150℃for 24 hours. Centrifuging at 8000rpm/min for 5min, washing the collected solid with tetrahydrofuran and ethanol for 3 times, and drying the white solid in a vacuum oven at 80 ℃ overnight to obtain the solid which is the COFs3 material.
Wherein 1 is TMB color development liquid, 2 is COFs1+TMB color development liquid, 3 is COFs2+TMB color development liquid, and 4 is COFs3+TMB color development liquid. As can be seen from fig. 1, the preparation process of COFs is shown in fig. 14, the color change of the solution 2 is most obvious, and the color change of other solutions is not obvious, which indicates that COFs1 has better catalytic effect on TMB, and the catalytic effect of oxidase of COFs2 and COFs3 is weaker than that of COFs1, so that the catalytic performance of oxidase of the material synthesized under the condition of example 1 is best. As can be seen from SEM and TEM images of fig. 2, COFs is a spherical structure, and further, it is known from the inspection analysis of fig. 3, 4, 5 and 6 that COFs has a uniform chemical structure and a regular crystal configuration, confirming that the method forms COFs materials.
Catalytic Activity test Using the COF prepared in example 1
(1) Catalytic Activity of oxidase
1mg of COFs material was taken, 1mL of an aqueous solution was added thereto, and the mixture was mixed well to prepare a 1mg/mL COFs suspension. And taking 500 mu LCFs suspension, adding 500 mu L of TMB solution, reacting for 0.5h in a dark place, photographing by a camera, and testing the absorbance at 650nm by using a functional enzyme-labeled instrument.
(2) Kinetic catalytic constant
500. Mu.L of COFs suspension was taken, TMB solutions (0, 10, 50, 100, 250, 500, 750, 1000, 1250, 1500, 1750, 2000. Mu.L) of different volumes were added respectively, water was added to a total volume of 2500. Mu.L, and the reaction was carried out in the dark for 0.5h. The absorbance at 650nm is measured by using a functional enzyme label instrument, and the catalytic kinetic curve of the COFs simulated enzyme is obtained by plotting TMB concentration and absorbance value. Detection of ascorbic acid Using the COF prepared in example 1
(1) Determination of a Standard Curve
COF (200 μl,1 mg/mL) and TMB (100 μl,0.3 mg/mL) were combined at 1:1, and reacting for 90min at room temperature. Standard solutions of different concentrations were prepared from standard products of ascorbic acid, and each solution was dissolved in a pure water solution to prepare a plurality of standard solutions of ascorbic acid. Standard solutions of different concentrations were added drop wise to the COFs-TMB system.
(2) Specific detection
Preparing a solution with concentration of 10mg/mL by using different types of competing substances (sodium chloride, potassium chloride, calcium chloride, glucose, mannose, glycine, cholesterol, phenylalanine and uric acid), preparing a standard mixed solution of 1mg/mL of ascorbic acid, mixing the different types of competing substances with the standard solution of 1mg/mL of ascorbic acid in equal proportion, and measuring a fluorescent signal after reacting for 5 min.
1) Preparing standard solutions of different preparations of ascorbic acid by using standard substances of the ascorbic acid, and respectively dissolving the standard solutions in pure water solution to prepare a plurality of standard solutions of the ascorbic acid;
2) Preparing a standard mixed solution of various types of ascorbic acid by using different types of competing substances to prepare a concentration of 10mg/mL and mixing the different types of competing substances with the standard solution of the ascorbic acid;
3) Dripping standard solutions with different concentrations into the covalent organic framework material solution, photographing by using a camera after reacting for 5min, reading an ultraviolet signal by using a multifunctional enzyme-labeled instrument, and establishing a linear relation between the concentration of ascorbic acid and the ultraviolet signal;
4) And (3) dripping standard mixed solutions of different types of competing substance solutions and ascorbic acid into the covalent organic framework material solution, photographing by a camera after reacting for 5min, reading ultraviolet signals by a multifunctional enzyme-labeled instrument, and comparing ultraviolet signal changes in the presence or absence of the ascorbic acid.
The reaction system was subjected to different times, different pH and reaction temperature to obtain the optimal reaction time (FIG. 9), pH (FIG. 10) and temperature (FIG. 11). Standard solutions of different concentrations were prepared from standard products of ascorbic acid, and each solution was dissolved in a pure water solution to prepare a plurality of standard solutions of ascorbic acid. Under the optimal reaction condition, standard solutions with different concentrations are dripped into the COFs-TMB system, ultraviolet signals are read by a multifunctional enzyme-labeled instrument, and a linear relation between the concentration of the ascorbic acid and the ultraviolet signals is established (figure 12). The results of fig. 13 show that the sensor of the present invention has satisfactory specificity.
Effervescent tablets based on COFs nanoenzyme of example 1 and recovery experiments of ascorbic acid in strawberry samples
Grinding appropriate amount of Vc effervescent tablet into powder with a mortar, accurately weighing 5.00g of powder into a 100mL beaker, adding a certain amount of Vc standard substance solution to make the final concentration of Vc standard substance solution be 3.33,33.30,100.00 mug/g respectively, and mixing uniformly. 50mL of oxalic acid solution (20 g/L) is added, the mixture is transferred to a 100mL volumetric flask after being fully dissolved, the volume is fixed to 100mL by using 20g/L of oxalic acid solution, and the solution is filtered for standby.
And taking a proper amount of strawberry samples and homogenizing by a homogenizer. Accurately weighing 5.00g of homogenized sample into a 100mL beaker, adding a certain amount of Vc standard solution to make the final concentration of the Vc standard solution be 3.33,33.30,100.00 mug/g respectively, and uniformly mixing. 50mL of oxalic acid solution (20 g/L) is added, the mixture is transferred to a 100mL volumetric flask after being fully dissolved, the volume is fixed to 100mL by using 20g/L of oxalic acid solution, and the solution is filtered for standby.
TABLE 2 Vc-labeled recovery experiment in actual sample
From Table 2, it can be found that the recovery rate of Vc detected by the method of the embodiment of the present application is consistent with that of the national standard, which proves that the method has great potential in practical application.
The foregoing is merely a specific embodiment of the application to enable one skilled in the art to understand or practice the application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A covalent organic framework material, wherein the chemical composition of the covalent organic framework material comprises:
terephthalaldehyde and 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin; wherein, the liquid crystal display device comprises a liquid crystal display device,
the weight ratio of the terephthalaldehyde to the 5,10,15, 20-tetra (4-aminophenyl) porphyrin is 2-4: 5.
2. the covalent organic framework material of claim 1, wherein the weight ratio of terephthalaldehyde to 5,10,15, 20-tetrakis (4-aminophenyl) porphyrin is 3:5.
3. use of the covalent organic framework material of claim 1 or 2 for the detection of ascorbic acid.
4. A method for preparing a covalent organic framework material according to claim 1 or 2, comprising:
mixing terephthalaldehyde, 5,10,15, 20-tetra (4-aminophenyl) porphyrin and a solvent, and heating under the condition of a set temperature to obtain a reaction solution;
and centrifuging and drying the reaction liquid to obtain the covalent organic framework material.
5. The method of claim 4, wherein the set temperature is 50 to 150 ℃.
6. The method of claim 4 or 5, wherein the set temperature is 90 ℃.
7. The method of claim 4, wherein the heating is for a period of 24 to 72 hours.
8. The method of claim 4 or 7, wherein the heating is for a period of 48 hours.
9. The method according to claim 4, wherein the solvent is dimethyl sulfoxide, and the volume V of dimethyl sulfoxide and the weight M of terephthalaldehyde satisfy the relationship: v: m=1 to 3:1.
10. the method according to claim 9, wherein the volume V of dimethyl sulfoxide and the weight M of terephthalaldehyde satisfy the relationship: v: m=1: 1.
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| CN117497081A (en) * | 2023-12-29 | 2024-02-02 | 北京市农林科学院 | Logic gate construction based on porphyrin COF fipronil and application thereof |
| CN117659432A (en) * | 2024-02-01 | 2024-03-08 | 四川大学 | Porous nickel porphyrin-based hydrogen bond organic framework material and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117497081A (en) * | 2023-12-29 | 2024-02-02 | 北京市农林科学院 | Logic gate construction based on porphyrin COF fipronil and application thereof |
| CN117497081B (en) * | 2023-12-29 | 2024-04-05 | 北京市农林科学院 | Logic gate construction based on porphyrin COF fipronil and application thereof |
| CN117659432A (en) * | 2024-02-01 | 2024-03-08 | 四川大学 | Porous nickel porphyrin-based hydrogen bond organic framework material and preparation method and application thereof |
| CN117659432B (en) * | 2024-02-01 | 2024-04-02 | 四川大学 | Porous nickel porphyrin-based hydrogen bond organic framework material and preparation method and application thereof |
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