CN114702953A - Fluorescence probe based on lanthanide ion hybrid covalent organic framework material, preparation method and application - Google Patents
Fluorescence probe based on lanthanide ion hybrid covalent organic framework material, preparation method and application 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 36
- 239000000463 material Substances 0.000 title claims abstract description 33
- 239000000523 sample Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 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
- 238000009396 hybridization Methods 0.000 claims abstract description 5
- 150000002466 imines Chemical class 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 10
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- 238000005406 washing Methods 0.000 claims description 7
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- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000203 mixture 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
- 238000001514 detection method Methods 0.000 claims description 5
- 229940014800 succinic anhydride Drugs 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000003756 stirring 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
- -1 europium ions Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- PCJQOISZFZOTRH-UHFFFAOYSA-K trichloroeuropium;hydrate Chemical compound O.[Cl-].[Cl-].[Cl-].[Eu+3] PCJQOISZFZOTRH-UHFFFAOYSA-K 0.000 claims description 2
- 150000002601 lanthanoid compounds Chemical class 0.000 claims 2
- 229910052693 Europium Inorganic materials 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000007850 fluorescent dye Substances 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 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 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 5
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- 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 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000009471 action Effects 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
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- 239000001257 hydrogen Substances 0.000 description 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 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
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 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"
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Abstract
The invention discloses a fluorescence probe based on lanthanide ion hybridization covalent organic framework material, a preparation method and application thereof. The lanthanide ion hybrid covalent organic framework material is obtained by a coordination reaction of a carboxylated imine covalent organic framework and europium chloride hexahydrate; the lanthanide ion hybrid covalent organic framework material not only improves the sensitivity by extracting and enriching the strong affinity of the covalent organic framework to target molecules, but also forms a new fluorescence center by utilizing the coordination of carboxylate radicals and lanthanide ions, thereby reducing the environmental interference. The constructed lanthanide ion hybrid 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 lanthanide ion hybridization covalent organic framework material-based fluorescent probe, and a preparation method and application thereof.
Background
Lanthanide rare earth metal ion (Ln)3+) Has the characteristics of sharp characteristic fluorescence peak, high color purity and resolution, large Stokes displacement, contribution to eliminating external interference and the like, and is an excellent material for preparing a fluorescent probe[1]. But due to Ln3+The ion has a smaller molar absorption coefficient, and f-f forbidden transition weakens the absorption capacity of the ion, and the ion can be excited only in a plurality of special wave bands, so that the application of the ion is limited. With lanthanide ions (Ln)3+) Or the lanthanide series luminescent complex is taken as an object, an organic material or an inorganic material is taken as a main matrix, and the lanthanide series hybrid luminescent material assembled by the interaction of the object and the organic material can improve the luminescent intensity, broaden the excitation spectrum and improve the thermal stability and the mechanical stability[2]. However, there are still some problems in the field of lanthanide organic/inorganic hybridization: (1) the photostability of these hybrid systems, especially in aqueous environments, is to be further improved. Water molecules can form coordination with lanthanide ions, and quenching effects caused by vibration modes of coordinated water molecules can weaken the emission intensity of the lanthanide ions. (2) In complex systems or actual samples, the anti-interference detection capability of the lanthanide series hybrid luminescent material 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 certain luminescent property due to a large pi-conjugated system[5]Its periodic structure allows the introduction of specific targets to increase specificity. Compared with the traditional small molecule chemical sensor, the sensor has the advantages thatThe valuable organic framework materials are insoluble in water and common organic solvents, and are convenient to separate, regenerate and reuse. In addition, the covalent organic framework has large surface area, can interact with a target, and has adjustable electronic and photophysical properties[6]。
Based on the above, the invention provides a fluorescence probe based on lanthanide ion hybrid covalent organic framework material, which utilizes the coordination of a covalent organic framework surface functional group and lanthanide ions to improve the light stability of the hybrid material, and utilizes the interaction force of the covalent organic framework surface functional group and a target object 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 overcome the defects of the prior art, the invention provides a fluorescence probe based on a lanthanide ion hybrid covalent organic framework material, a preparation method and application thereof, and aims to realize the rapid synthesis and application of the lanthanide ion hybrid covalent organic framework material.
The invention is realized by the following technical scheme:
the invention has the following advantages and effects:
1. the invention adopts a carboxylated covalent organic framework as a reactant to prepare the lanthanide ion hybrid covalent organic framework material, and the carboxylate radical on the surface of the covalent organic framework coordinates with lanthanide ions, thereby providing the following 3 benefits: 1) increased stability and uniformity of lanthanide ions in the product; 2) the coordination of water molecules and lanthanide ions is reduced, thereby reducing the quenching effect caused by the vibration mode of the coordinated water molecules.
2. According to the invention, carboxylic acid radicals are modified on the surface of a covalent organic framework through a hydrolysis reaction of succinic anhydride, so that the carboxylic acid radicals can generate electrostatic interaction and van der Waals force with amino and hydroxyl of target compound molecules, and selective enrichment of the target compounds is realized.
3. The imine covalent organic framework has the fluorescence influence, and the ratio type fluorescent probe is constructed by hybridization with lanthanide ions, so that the environmental interference is reduced.
Drawings
FIG. 1 is a schematic diagram of the preparation of homemade lanthanide ion hybrid covalent organic framework material.
Detailed Description
The invention discloses a fluorescence probe based on lanthanide ion hybrid covalent organic framework material and a preparation method and application thereof.
The preparation method comprises the following specific steps:
1) uniformly mixing amine monomers containing hydroxyl and p-toluenesulfonic acid to obtain viscous salt, adding a certain amount of aldehyde monomers, uniformly mixing, adding a small amount of deionized water into the mixture to form dough, 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) Ultrasonically dispersing the solid obtained in the step 2) in anhydrous acetone solution of succinic anhydride, heating and stirring for reaction, wherein the solid concentration in the anhydrous acetone is 5g L-1The concentration of succinic anhydride is 2mol L-1The 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 55 deg.C, and dispersing in 0.01mol L-1The reaction is carried out at room temperature in the europium chloride hexahydrate solution, and the concentration of the precipitate in the europium chloride hydrate solution is 8g L-1The reaction time was 12 hours at room temperature.
5) And (3) centrifugally separating the solid obtained in the step 4), washing the solid for 3 times by using deionized water, and drying the solid for 12 hours at the temperature of 90 ℃ to obtain the lanthanide ion hybrid covalent organic framework material.
The technical scheme of the invention is further explained by combining the attached drawings of the specification:
the fluorescent probe based on the novel lanthanide ion hybrid covalent organic framework material is prepared, and has high enrichment efficiency by selectively enriching tetracycline in a water sample through simple solid-phase extraction. And then analyzing and determining the concentration of the tetracycline under the fluorescent condition.
Fig. 1 is a schematic diagram 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 were mixed uniformly to obtain a viscous salt, 48.6g of trimesic aldehyde was added and mixed uniformly, 10mL of deionized water was added to form a dough, and the dough was heated at 170 ℃ for 5 min. The crude product was washed with a large amount of hot water, N-dimethylformamide dimethyl acetal and acetone in this order, centrifuged, and dried at 55 ℃ for 12 hours to obtain a covalent organic framework powder. 50mg of covalent organic framework powder was dispersed in 10mL of a solution containing 2mol L-1Stirring the mixture for 24 hours at the temperature of 60 ℃ in anhydrous acetone solution of succinic anhydride, centrifugally collecting precipitates, and washing the precipitates to obtain the carboxylated covalent organic framework. 80mg of carboxylated covalent organic framework powder was dispersed in10mL of a solution of europium chloride hexahydrate (0.01mol L)-1) Then, the mixture was stirred 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 the novel lanthanide ion hybridized covalent organic framework material is as follows:
step one, enrichment: 10mg of lanthanide ion hybridized covalent organic framework material was directly dispersed into 10mL of water sample. 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 of deionized water was added and sonicated for 5 minutes to disperse the solids evenly.
And step two, detection: analysis of tetracycline was performed on the erburg FLS920 spectrophotometer. And (3) measuring the solution obtained in the first step under the action of excitation light of 380nm, observing an emission spectrum, and calculating the concentration of tetracycline.
Finally, it should also be noted that the above-mentioned list is only a specific embodiment of the invention. It is obvious that the present invention is not limited to the above embodiments, but many variations are possible, and all variations that can be derived or suggested by 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 (6)
1. A fluorescence probe based on lanthanide ion hybridization covalent organic framework material is characterized in that the structural formula is shown as the following figure:
2. a preparation method of a fluorescence probe based on lanthanide ion hybrid covalent organic framework material is characterized in that a carboxylated imine covalent organic framework is adopted as a hybrid material to perform coordination reaction with europium ions to obtain the fluorescence probe based on lanthanide ion hybrid covalent organic framework.
3. The preparation method of the fluorescence probe based on lanthanide ion hybrid covalent organic framework material as claimed in claim 2, characterized in that the preparation method specifically comprises the following steps:
1) adding an aldehyde monomer into a mixture of an amine monomer and p-toluenesulfonic acid, adding a small amount of deionized water, and heating for reaction;
2) washing the precipitate obtained in the step 1) with hot water, N-dimethylformamide dimethyl acetal and acetone in sequence, and drying;
3) dispersing the solid obtained in the step 2) in anhydrous acetone solution of succinic anhydride, and heating and stirring for reaction;
4) centrifugally separating the solid obtained in the step 3), washing, drying, dispersing in a lanthanide compound solution, and stirring at room temperature for reaction;
5) and 4) centrifugally separating the solid obtained in the step 4), washing and drying to obtain the lanthanide ion hybrid covalent organic framework material.
4. The method for preparing a fluorescence probe based on lanthanide ion hybrid covalent organic framework material as claimed in claim 3, wherein in step 1), the amine monomer contains hydroxyl functional group.
5. The method for preparing a fluorescence probe based on lanthanide ion hybrid covalent organic framework material as claimed in claim 3, wherein in said step 4), said lanthanide compound is europium chloride hydrate.
6. The application of the fluorescence probe prepared from the lanthanide ion hybrid covalent organic framework material as claimed in claim 1 in extraction and detection of tetracycline in a water sample.
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