CN114702953B - Fluorescent probe based on lanthanide ion hybridization covalent organic framework material and preparation method and application thereof - Google Patents
Fluorescent probe based on lanthanide ion hybridization covalent organic framework material and preparation method and application thereof Download PDFInfo
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- 239000013310 covalent-organic framework Substances 0.000 title claims abstract description 42
- 229910021644 lanthanide ion Inorganic materials 0.000 title claims abstract description 29
- 239000000463 material Substances 0.000 title claims abstract description 28
- 238000009396 hybridization Methods 0.000 title claims abstract description 21
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000004098 Tetracycline Substances 0.000 claims abstract description 7
- 229960002180 tetracycline Drugs 0.000 claims abstract description 7
- 229930101283 tetracycline Natural products 0.000 claims abstract description 7
- 235000019364 tetracycline Nutrition 0.000 claims abstract description 7
- 150000003522 tetracyclines Chemical class 0.000 claims abstract description 7
- AWDWVTKHJOZOBQ-UHFFFAOYSA-K europium(3+);trichloride;hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Eu+3] AWDWVTKHJOZOBQ-UHFFFAOYSA-K 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 229940014800 succinic anhydride Drugs 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ZGDMDBHLKNQPSD-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(N)C(O)=C1 ZGDMDBHLKNQPSD-UHFFFAOYSA-N 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 150000002466 imines Chemical class 0.000 abstract description 2
- 230000035945 sensitivity Effects 0.000 abstract 2
- 239000000284 extract Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 7
- 229910052747 lanthanoid Inorganic materials 0.000 description 6
- 150000002602 lanthanoids Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- -1 Lanthanide rare earth metal ion Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
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- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- G01N21/6428—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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
-
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention discloses a fluorescent probe based on lanthanide ion hybridization covalent organic framework material, a preparation method and application thereof. The lanthanide ion hybridization covalent organic framework material is obtained by coordination reaction of carboxylated imine covalent organic frameworks and europium chloride hexahydrate; the lanthanide ion hybridization covalent organic framework material not only extracts and enriches the target molecules with strong affinity through the covalent organic framework and improves the sensitivity, but also forms a new fluorescence center by utilizing the coordination of carboxylate radical and lanthanide ion, thereby reducing the environmental interference. The constructed lanthanide ion hybridization covalent organic framework material can be used for constructing a high-performance fluorescent probe for detecting tetracycline with high sensitivity, high selectivity and high stability.
Description
Technical Field
The invention belongs to the technical field of environmental detection, and particularly relates to a fluorescent probe based on lanthanide ion hybridization covalent organic framework material, a preparation method and application thereof.
Background
Lanthanide rare earth metal ion (Ln) 3+ ) Has the characteristics of sharp characteristic fluorescence peak, extremely high color purity and resolution, larger Stokes displacement, contribution to eliminating external interference and the like, and is an excellent material for preparing fluorescent probes [1] . But due to Ln 3+ Has a small molar absorptivity per se andthe f-f forbidden transition weakens the light absorption capacity of the ion system, and can be excited only in a few special wave bands, thereby limiting the application of the ion system. With ions of the lanthanide series (Ln 3+ ) Or lanthanide luminescent complex as object, organic material or inorganic material as main matrix, and lanthanide hybrid luminescent material assembled by interaction of main object and object can improve luminous intensity, widen excitation spectrum, and improve thermal stability and mechanical stability [2] . However, there are still some problems in the field of lanthanide organic/inorganic hybridization: (1) The photostability of these hybrid systems, in particular in aqueous environments, is to be further improved. The water molecules form coordination with the lanthanide ions, and quenching effect caused by vibration modes of the coordinated water molecules weakens the emission intensity of the lanthanide ions. (2) In complex systems or actual samples, the anti-interference detection capability of lanthanide hybrid luminescent materials needs to be improved [3] 。
The covalent organic framework material is a crystalline porous polymer composed of light elements (such as hydrogen, carbon, oxygen, nitrogen, silicon and the like), has the remarkable characteristics of large surface area, adjustable pore diameter, good thermal stability, good chemical stability and changeable structure, and is concerned by researchers in various fields [4] . The covalent organic framework crystal structure has a large pi-conjugated system to ensure that the covalent organic framework crystal structure has certain luminous performance [5] Its periodic structure allows the introduction of specific targets to increase specificity. Compared with the traditional small molecule chemical sensor, the covalent organic framework material is insoluble in water and common organic solvents, and is convenient for separation, regeneration and reuse. In addition, covalent organic frameworks have a large surface area, can interact with targets, and are tunable in electronic and photophysical properties [6] 。
Based on the fluorescent probe, the fluorescent probe based on the lanthanide ion hybridization covalent organic framework material is provided, the coordination of the covalent organic framework surface functional group and the lanthanide ion is utilized, the photostability of the hybridization material is improved, and the interaction force between the covalent organic framework surface functional group and the target object is utilized to improve the anti-interference detection capability of the material.
Reference to the literature
[1]Lidia Armelao,Silvio Quici,Francesco Barigelletti,et al.Design of luminescent lanthanide complexes:From molecules to highly efficient photo-emitting materials.Coordination Chemistry Reviews:2010,254(5-6):487-505.
[2]Tianying Sun,Yaobin Gao,Yangyang Du,et al.Recent Advances in Developing Lanthanide Metal-Organic Frameworks for Ratiometric Fluorescent Sensing.Frontiers in chemistry:2020,8:624592.
[3]Xi Chen,Yang Xu,and Huanrong Li.Lanthanide organic/inorganic hybrid systems:Efficient sensors for fluorescence detection.Dyes and Pigments:2020,178:108386.
[4]Xiao Feng,Xuesong Ding,and Donglin Jiang.Covalent organic frameworks.Chemical Society reviews:2012,41(18):6010-22.
[5]W.K.Haug,E.M.Moscarello,E.R.Wolfson,et al.The luminescent and photophysical properties ofcovalent organic frameworks.Chemical Society reviews:2020,49(3):839-864.
[6]Tina Skorjanc,Dinesh Shetty,and Matjaz Valant.Covalent Organic Polymers and Frameworks for Fluorescence-Based Sensors.ACS sensors:2021,6(4):1461-1481.
Disclosure of Invention
In order to solve the defects in the prior art, the invention provides a fluorescent probe based on lanthanide ion hybridization covalent organic framework materials, a preparation method and application thereof, and aims to realize rapid synthesis and application of the lanthanide ion hybridization covalent organic framework materials.
The invention is realized by the following technical scheme:
the invention has the following advantages and effects:
1. the lanthanide ion hybridization covalent organic framework material is prepared by adopting the carboxylation covalent organic framework as a reactant, and the carboxylate radical on the surface of the covalent organic framework is coordinated with the lanthanide ion, so that the following 3 advantages are provided: 1) The stability and uniformity of lanthanide ions in the product are improved; 2) The coordination of water molecules and lanthanide ions is reduced, so that the quenching effect caused by the vibration mode of the coordinated water molecules is reduced.
2. According to the invention, carboxylic acid radicals are modified on the surface of the covalent organic framework through hydrolysis reaction of succinic anhydride, so that electrostatic action and Van der Waals force can be generated between the carboxylic acid radicals and amino and hydroxyl of target compound molecules, and selective enrichment of the target compounds is realized.
3. The imine covalent organic frameworks themselves have a fluorescent effect, and the environmental interference is reduced by constructing a ratio-type fluorescent probe by hybridization with lanthanide ions.
Drawings
FIG. 1 is a schematic illustration of the preparation of a homemade lanthanide ion hybrid covalent organic framework material.
Detailed Description
The invention discloses a fluorescent probe based on lanthanide ion hybridization covalent organic framework material, a preparation method and application thereof.
The preparation method comprises the following specific preparation steps:
1) Uniformly mixing amine monomers containing hydroxyl groups with p-toluenesulfonic acid to obtain viscous salt, adding quantitative aldehyde monomers, uniformly mixing, adding a small amount of deionized water into the mixture to form a dough shape, and heating at 170 ℃ for 5min, wherein the concentration of the amine monomers in the mixture is 1.5 times that of the aldehyde monomers.
2) Washing the precipitate obtained in the step 1) with a large amount of hot water, N-dimethylformamide dimethyl acetal and acetone in sequence, centrifuging, and drying at 55 ℃ for 12 hours.
3) Dispersing the solid obtained in the step 2) in anhydrous acetone solution of succinic anhydride by ultrasonic wave, heating and stirring for reaction, wherein the concentration of the solid in the anhydrous acetone is 5g L -1 Succinic anhydride concentration of 2mol L -1 The reaction temperature is 60 ℃ and the reaction time is 24 hours;
4) Centrifuging the solid obtained in step 3), washing with anhydrous propanol, drying at 55deg.C, and dispersing in 0.01mol L -1 In the europium chloride hexahydrate solution, the concentration of the precipitate in the europium chloride hexahydrate solution is 8g L -1 The reaction time at room temperature was 12 hours.
5) And (3) centrifugally separating the solid obtained in the step (4), washing the solid with deionized water for 3 times, and drying the solid at 90 ℃ for 12 hours to obtain the lanthanide ion hybridization covalent organic framework material.
The technical scheme of the invention is further described below with reference to the attached drawings in the specification:
the fluorescent probe based on the novel lanthanide ion hybridization covalent organic framework material is prepared, and tetracycline in a water sample is selectively enriched through simple solid-phase extraction, so that the fluorescent probe has high enrichment efficiency. And then analyzing and measuring the concentration of the tetracycline under the fluorescent condition.
Fig. 1 is a schematic diagram of the preparation of a self-made lanthanide ion hybrid covalent organic framework material, and the specific preparation process is as follows:
97.2g of 3,3' -dihydroxybenzidine and 430g of p-toluenesulfonic acid are uniformly mixed to obtain viscous salt, 48.6g of trimesic aldehyde is added and uniformly mixed, 10mL of deionized water is added to form a dough, and the mixture is heated at 170 ℃ for 5min. The crude product was washed sequentially with a large amount of hot water, N-dimethylformamide dimethyl acetal and acetone, centrifuged, and dried at 55℃for 12 hours to obtain a covalent organic framework powder. 50mg of the covalent organic framework powder was dispersed in 10mL of a solution containing 2mol L -1 Stirring the mixture in anhydrous acetone solution of succinic anhydride at 60 ℃ for 24 hours, centrifugally collecting precipitate, and cleaning to obtain carboxylated covalent organic frameworks. 80mg of carboxylated covalent organic framework powder was dispersed in 10mL of europium chloride hexahydrate solution (0.01 mol L) -1 ) In the above, stirring was carried out at room temperature for 12 hours. The precipitate was collected by centrifugation, washed three times with deionized water and dried at 90 ℃ for 12 hours.
The process of extracting tetracycline from water sample by using novel lanthanide ion hybridization covalent organic framework material is as follows:
first, enrichment: 10mg of lanthanide ion hybridized covalent organic framework material was dispersed directly into 10mL water samples. The mixture solution was sonicated for 5 minutes and then centrifuged at 6000rpm for 3 minutes to separate the two phases. After removing the supernatant, 0.5mL deionized water was added and sonicated for 5 minutes to disperse the solids uniformly.
Second, detecting: analysis of tetracycline was performed on an Edinburgh FLS920 spectrophotometer. And (3) measuring the solution obtained in the step one under the action of 380nm excitation light, observing an emission spectrum, and calculating the concentration of the tetracycline.
Finally, it should also be noted that the above list is merely a specific example of the invention. It is obvious that the present invention is not limited to the above embodiments, but many variations are possible, and all modifications which can be directly derived or suggested to a person skilled in the art from the disclosure of the present invention should be considered as the protection scope of the present invention.
Claims (3)
1. A fluorescent probe based on lanthanide ion hybridization covalent organic framework material, which is characterized in that the structural formula is shown in the following figure:
2. a method for preparing a fluorescent probe based on lanthanide ion hybridization covalent organic framework material as defined in claim 1, characterized in that 97.2g of 3,3' -dihydroxybenzidine and 430g of p-toluenesulfonic acid are uniformly mixed to obtain viscous salt, 48.6g of trimellitic aldehyde are added to be uniformly mixed, 10mL of deionized water is added to form dough, heating is carried out at 170 ℃ for 5min, the product is sequentially washed by a large amount of hot water, N-dimethylformamide dimethyl acetal and acetone, centrifugal separation is carried out, drying is carried out at 55 ℃ for 12h, covalent organic framework powder is obtained, 50mg of covalent organic framework powder is dispersed in 10mL of solution containing 2mol L -1 Stirring in anhydrous acetone solution of succinic anhydride at 60deg.C for 24 hr, centrifuging to collect precipitate, cleaning to obtain carboxylated covalent organic framework, dispersing 80mg carboxylated covalent organic framework powder in 10ml0.01 mol L -1 In europium chloride hexahydrate solution, stirring at room temperature for 12 hours, collecting the precipitate by centrifugation, washing three times with deionized water and drying at 90℃for 12 hours.
3. Use of a fluorescent probe based on lanthanide ion hybridization covalent organic framework material according to claim 1 for extraction and detection of tetracycline in water samples.
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