CN112159530A - Preparation and application of metal organic framework material - Google Patents
Preparation and application of metal organic framework material Download PDFInfo
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- CN112159530A CN112159530A CN202011170490.1A CN202011170490A CN112159530A CN 112159530 A CN112159530 A CN 112159530A CN 202011170490 A CN202011170490 A CN 202011170490A CN 112159530 A CN112159530 A CN 112159530A
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- G01N21/62—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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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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
- G01N21/62—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
Abstract
The invention discloses a preparation method of metal organic framework material and application technical scheme thereof, which comprises the step of adding zinc nitrate hexahydrate (Zn (NO)3)2·6H2Adding O), benzimidazole and 2, 6-dihydroxyterephthalic acid into a solution of N, N-dimethylacetamide (DMAc) and ethanol at a certain volume ratio according to a certain molar ratio, and synthesizing a metal organic framework material by adopting a solvothermal method, wherein the chemical formula of the metal organic framework material is C26H29N2O6Zn3The space group is C2/m, the method belongs to a triclinic system, a liquid fluorescence detection means is adopted to prepare a suspension of a compound, the p-nitrobenzene is selectively quenched, when the concentration of nitrobenzene reaches 120ppm, the quenching rate of the solution reaches 86.6%, and the compound can be used as a fluorescence probe for detecting nitrobenzene.
Description
Technical Field
The invention belongs to the field of synthesis of metal organic framework materials, and particularly relates to preparation of a metal organic framework material and application of the metal organic framework material in a selective fluorescent probe.
Background
Metal organic framework polymers (MOFs), a class of crystalline microporous materials with broad prospects, have attracted great interest under the promotion of coordination chemistry principles. Depending on the geometry of the organic ligand and the coordination mode of the inorganic metal ion or metal ion cluster, its structure can be tailored by the properties of interest. The coordination mode of the ions or metal ion clusters can be tailored to their structure by the properties of interest. Key characteristics in the structural features of MOFs are ultra-high porosity (up to 90% free volume) and ultra-high internal surface area, which extends beyond the langmuir surface area of 10000m2g-1. Due to the characteristics of stable structure and high porosity, the MOFs can be used for gas storage and separation,The aspects of catalysis, proton conduction, drug delivery and luminescence sensors play key roles.
Among the numerous reported luminescent materials, luminescent coordination polymers have recently been developed as potential chemical sensors due to their advantages of being easy to induce luminescence, diversity of structural and functional components, and various detection mechanisms. The detection of high explosives using luminescent MOFs sensors is probably one of its most promising applications. The detection of high explosives using luminescent MOFs sensors is probably one of its most promising applications. The detection of the high-energy materials plays a very important role in the aspects of anti-terrorist action, homeland safety, civil safety, environmental pollution and the like, so that the high-energy materials have the capabilities of directly saving human lives and protecting the environment. With the increasing terrorist activities worldwide, there is a need to focus more on and develop a fast, sensitive, and efficient method for detecting explosives. Some current detection methods, such as ion mobility spectrometry, various imaging techniques, etc., can make the detection sensitivity higher and increase the accuracy of the test, but they also have many disadvantages, most notably high cost and lack of portability, while optical sensing techniques are rapidly developed with their advantages of low cost, high speed, portability, etc.
As a viable luminescence sensor, the following requirements need to be met: first, the ability of the material to capture analyte molecules to a desired local concentration will contribute to the increased sensitivity, as the material needs to respond to the analyte in a given area. The sensitivity is improved. Second, an excellent sensor should be insensitive to non-targeted fluorescence quenching that may be caused by the test environment. The light quenching is not sensitive. Furthermore, chemical and physical stability is also required to enable efficient testing in extreme environments.
Metal coordination polymers are organic-inorganic crystalline hybrid materials assembled from metal cations and multidentate organic ligands, and have attracted much attention over the past few decades. The metal-organic coordination polymers have various classification modes according to different classification standards. Polymers have a wide variety of classifications. From the perspective of the central ion forming the complex, common complexes can be divided into three categories: transition metal complexes, alkali metal complexes, and rare earth metal complexes; from the perspective of spatial dimensions, common complexes can be classified into the following four types: zero-dimensional complexes, one-dimensional chain complexes, two-dimensional layered complexes and three-dimensional reticular complexes; from the functional point of view, the material can be divided into a luminous complex, a gas storage complex, a catalytic complex, a magnetic complex and the like; from a topological point of view, common complexes can be divided into two categories: single node and mixed node complexes. From the viewpoint of ligand selection, common complexes can be generally divided into complexes containing nitrogen heterocyclic organic ligands, complexes containing carboxylic acid organic ligands and mixed complexes containing more than one organic ligand. In fact, the rational selection of organic ligands plays a very important role in constructing complexes with novel structures and excellent performance.
Disclosure of Invention
The invention aims to provide a preparation method of a metal organic framework material and application of the metal organic framework material in the aspect of a selective fluorescent probe, and the technical scheme is as follows:
zinc nitrate hexahydrate (Zn (NO)3)2·6H2Adding O), benzimidazole and 2, 6-dihydroxyterephthalic acid into a mixed solution of N, N-dimethylacetamide (DMAc) and ethanol according to a certain molar ratio, and synthesizing a metal organic framework material by adopting a solvothermal method, wherein the chemical formula of the metal organic framework material is C26H29N2O6Zn3The space group is C2/m, belonging to the triclinic system.
The preparation method comprises the following steps:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxy terephthalic acid according to a molar ratio of 3: 0.6-1.2: 0.4-0.9, adding into a beaker in sequence, adding N, N-dimethylacetamide (DMAc), and carrying out ultrasonic treatment to fully dissolve the N, N-dimethylacetamide.
S2: and (3) sucking 5mL of the solution obtained in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing down the solution, putting the solution into an oven, reacting for 24-48 h at 80-150 ℃, generating red blocky crystals, filtering, and drying for 8h at 65 ℃ to obtain the metal-organic framework material.
Preferably, the zinc nitrate hexahydrate (Zn (NO) of the step S13)2·6H2O), benzimidazole and 2, 6-dihydroxy terephthalic acid in a molar ratio of 3: 0.6-0.9: 0.4 to 0.6.
Preferably, the reaction temperature in the step S2 is 80 to 120 ℃.
Preferably, the reaction time in the step S2 is 24-36 h.
The invention has the following beneficial effects:
(1) the metal organic framework material prepared by the invention has the advantages of simple preparation method, easily obtained raw materials, higher chemical stability and good fluorescence emission performance.
(2) The metal organic framework material prepared by the invention has the excellent characteristics of high sensitivity, good selectivity, reusability and the like in the process of detecting nitrobenzene, and has good application prospect.
Drawings
FIG. 1 is an XRD pattern of a metal organic framework material prepared according to an embodiment of the present invention;
FIG. 2 is a FI-IR spectrum of a metal organic framework material prepared according to an example of the present invention;
FIG. 3 is a TG spectrum of a metal organic framework material prepared by an example of the present invention;
FIG. 4 is a liquid fluorescence spectrum of the metal organic framework material prepared in example 6 of the present invention in different solvents;
FIG. 5 is a liquid fluorescence spectrum of the metal organic framework material prepared in example 6 of the present invention in different concentrations of nitrobenzene.
FIG. 6 is a titration curve of p-nitrobenzene as a metal organic framework material prepared in example 6 of the present invention.
Detailed Description
The following describes embodiments of the present invention in detail, which are implemented on the premise of the technical solution of the present invention, and detailed embodiments and specific operation procedures are provided, but the scope of the present invention is not limited to the following embodiments.
Example 1
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acid in a molar ratio of 3: 0.6: 0.4 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 24 hours at 80 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Example 2
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acid in a molar ratio of 3: 1.2: 0.9 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 48 hours at 150 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Example 3
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acidAccording to a molar ratio of 3: 0.7: 0.5 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 30 hours at 90 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Example 4
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acid in a molar ratio of 3: 0.8: 0.6 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 36 hours at 100 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Example 5
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acid in a molar ratio of 3: 1.0: 0.8 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 36 hours at 120 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Example 6
A preparation method of a metal organic framework material comprises the following specific preparation processes:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxyterephthalic acid in a molar ratio of 3: 0.6: 0.45 was added to the beaker in sequence, followed by addition of N, N-dimethylacetamide (DMAc) and sonication to dissolve it sufficiently.
S2: and (3) sucking 5mL of the solution in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing the solution, putting the solution into an oven, reacting for 24 hours at 100 ℃, generating red blocky crystals, filtering the crystals, and drying the crystals for 8 hours at 65 ℃ to obtain the metal-organic framework material.
Performance test experiments: firstly, 2mg of the compound crystal is ground into powder in a mortar, the powder is dispersed in 3mL of N, N-dimethylformamide, N-dimethylacetamide, methanol, ethanol, dimethyl sulfoxide, water, tetrahydrofuran, acetonitrile and nitrobenzene solvents, then ultrasonic oscillation is carried out for 30min, and liquid fluorescence measurement shows that the suspension has a strong fluorescence emission peak at 448nm under the excitation wavelength of 280-330 nm. The compound can be selectively quenched by p-nitrobenzene fluorescence, as shown in figure 4; the compound was then added to various concentrations of a linear basic solvent, and when the concentration of nitrobenzene reached 120ppm, the fluorescence quenching rate of the solution reached 86.6%, as shown in FIG. 5.
Comparative example 1
Prepared according to the method described in the examples in the patent literature (CN 106749348B).
Claims (6)
1. A metal organic framework material is prepared by mixing zinc nitrate hexahydrate (Zn (NO)3)2·6H2Adding O), benzimidazole and 2, 6-dihydroxyterephthalic acid into a mixed solution of N, N-dimethylacetamide (DMAc) and ethanol according to a certain molar ratio, and synthesizing a metal organic framework material by adopting a solvothermal method, wherein the chemical formula of the metal organic framework material is C26H29N2O6Zn3The space group is C2/m, belonging to the triclinic system.
2. The method for preparing a metal-organic framework material according to claim 1, comprising the following steps:
s1: zinc nitrate hexahydrate (Zn (NO)3)2·6H2O), benzimidazole and 2, 6-dihydroxy terephthalic acid according to a molar ratio of 3: 0.6-1.2: 0.4-0.9, sequentially adding the mixture into a beaker, adding N, N-dimethylacetamide (DMAc), and carrying out ultrasonic treatment to fully dissolve the mixture;
s2: and (3) sucking 5mL of the solution obtained in the step S1 by using a dropper, adding the solution into a glass bottle with a bottle cap, then adding 1mL of absolute ethyl alcohol solution, screwing down the solution, putting the solution into an oven, reacting for 24-48 h at 80-150 ℃, generating red blocky crystals, filtering, and drying for 8h at 65 ℃ to obtain the metal-organic framework material.
3. The method of claim 1 or 2, wherein the zinc nitrate hexahydrate (Zn (NO) is3)2·6H2O), benzimidazole and 2, 6-dihydroxy terephthalic acid in a molar ratio of 3: 0.6-0.9: 0.4 to 0.6.
4. The method of claim 1 or 2, wherein the reaction temperature is 80-120 ℃.
5. The preparation method of the metal organic framework material as claimed in claim 1 or 2, wherein the reaction time is 24-36 h.
6. The application of the metal organic framework material as claimed in claim 1, wherein the fluorescent sensing material for detecting nitrobenzene is prepared by a liquid fluorescence detection method to prepare a suspension of a compound, and the fluorescence of p-nitrobenzene is selectively quenched, wherein when the concentration of nitrobenzene reaches 120ppm, the fluorescence quenching rate of the solution reaches 86.6%, and the compound can be used as a fluorescent probe for detecting nitrobenzene.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115181280A (en) * | 2022-06-08 | 2022-10-14 | 河北大学 | Preparation method, application and recycling method of metal-organic framework material MIL-101 (Fe) |
| CN115212923A (en) * | 2021-04-16 | 2022-10-21 | 鲁东大学 | Chain Mn (II) coordination polymer visible-light-driven photocatalyst containing mixed organic ligand and preparation method thereof |
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| CN105246906A (en) * | 2013-05-27 | 2016-01-13 | 英国贝尔法斯特女王大学 | Process for the preparation of a metal-organic compound |
| CN106749348A (en) * | 2016-11-22 | 2017-05-31 | 南开大学 | A kind of metal-organic framework material and preparation method and application |
| US20170166805A1 (en) * | 2014-07-15 | 2017-06-15 | Halliburton Energy Services, Inc. | Metal-Organic Frameworks as Encapsulating Agents |
| CN109879897A (en) * | 2019-04-04 | 2019-06-14 | 延安大学 | Macropore complex of transition metal containing nitronic acid and preparation method and application |
| CN110359295A (en) * | 2019-06-27 | 2019-10-22 | 东华大学 | A kind of preparation method of multi-functional long wavelength's long-life phosphors cotton fabric based on Cd-MOF |
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2020
- 2020-10-28 CN CN202011170490.1A patent/CN112159530A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105246906A (en) * | 2013-05-27 | 2016-01-13 | 英国贝尔法斯特女王大学 | Process for the preparation of a metal-organic compound |
| US20170166805A1 (en) * | 2014-07-15 | 2017-06-15 | Halliburton Energy Services, Inc. | Metal-Organic Frameworks as Encapsulating Agents |
| CN106749348A (en) * | 2016-11-22 | 2017-05-31 | 南开大学 | A kind of metal-organic framework material and preparation method and application |
| CN109879897A (en) * | 2019-04-04 | 2019-06-14 | 延安大学 | Macropore complex of transition metal containing nitronic acid and preparation method and application |
| CN110359295A (en) * | 2019-06-27 | 2019-10-22 | 东华大学 | A kind of preparation method of multi-functional long wavelength's long-life phosphors cotton fabric based on Cd-MOF |
Non-Patent Citations (1)
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| HU X. L. ET AL.: "Assembly of Zn-metal organic frameworks based on a N-rich ligand: selective sorption for CO2 and luminescence sensing of nitro explosives", 《RSC ADVANCES》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115212923A (en) * | 2021-04-16 | 2022-10-21 | 鲁东大学 | Chain Mn (II) coordination polymer visible-light-driven photocatalyst containing mixed organic ligand and preparation method thereof |
| CN115181280A (en) * | 2022-06-08 | 2022-10-14 | 河北大学 | Preparation method, application and recycling method of metal-organic framework material MIL-101 (Fe) |
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