CN106397467B - A kind of metal-organic framework functional fluorescence material, preparation method and applications - Google Patents
A kind of metal-organic framework functional fluorescence material, preparation method and applications Download PDFInfo
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- CN106397467B CN106397467B CN201610791662.4A CN201610791662A CN106397467B CN 106397467 B CN106397467 B CN 106397467B CN 201610791662 A CN201610791662 A CN 201610791662A CN 106397467 B CN106397467 B CN 106397467B
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- organic framework
- fluorescence material
- dimethylformamide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic System without C-Metal linkages
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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
- 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
- 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
Abstract
The present invention provides a kind of metal organic framework functional fluorescence material, the structural formula of the fluorescent material is [Eu12(FUM)18](H2O)8.Metal organic framework functional fluorescence material provided by the invention using atom centered on europium, has high-specific surface area, while have excellent fluorescence property again：There is the Stokes shift that bright and lustrous, fluorescence lifetime is long, larger.In the recognition detection applied to explosive small molecule, alternative identification TNP explosive small molecules, it is even more important that there is high sensitivity, to concentration 10‑8The explosive small molecule of M still has response.As detection probe, can be recycled.
Description
Technical field
The present invention relates to a kind of metal aggregates, and in particular to a kind of metal-organic framework materials, preparation method and its should
With belonging to fluoroscopic examination field.
Background technology
With society develop, science and technology progress, substance detect in life science, environmental science, medicine and nuclear industry
Etc. various fields have increasingly important role.In numerous detection methods, fluoroscopic examination with it flexibly and fast, it is highly sensitive
The characteristics of spending has obtained extensive concern.
Metal-organic framework materials are to be formed by inorganic metal ion or cluster with organic ligand by Chemical self-assembly,
With higher specific surface area and porosity, and regulatable pore size, in gas storage, adsorbing separation, catalysis, change
It learns sensing and drug transmission etc. and possesses wide application prospect.
In the fields such as the recognition detection of explosive small molecule, not only need fluorescent material alternative identification TNP etc. quick-fried
Fried object small molecule is more desirable to it and can realize respond in the case of low explosive little molecular concentration, that is, has high sensitivity.
In consideration of it, urgently proposing a kind of fluorescent material, it can be achieved that Selective recognition TNP explosive small molecules at present, and have
There is good sensitivity.
Invention content
The technical problems to be solved by the invention provide a kind of achievable Selective recognition TNP explosive small molecules, and have
There is the fluorescent material of good sensitivity, to meet the demand of the recognition detection of explosive small molecule etc..
Of the existing technology in order to solve the problems, such as, the present invention provides a kind of metal-organic framework functional fluorescences
Material, the structural formula of the fluorescent material is [Eu12(FUM)18](H2O)8, hereinafter referred to as Eu-FUM.
Preferably, the duct of the fluorescent material is 1D ducts.
Preferably, each metal europium ion of the fluorescent material respectively with the oxygen atom and hydrone on ligand carboxyl
Link.
Preferably, each metal europium ion nine of the fluorescent material is coordinated, respectively with the oxygen atom on 6 ligand carboxyls
And 1 moisture sublink.
It is further preferred that the on-link mode (OLM) of the metal europium ion and the oxygen atom on the ligand carboxyl is an oxygen
Atom and an europium ion link, alternatively, an oxygen atom and two europium ion links.
The present invention also provides the methods for preparing above-mentioned metal-organic framework functional fluorescence material, include the following steps：
Using 2- fluobenzoic acids as conditioning agent, fumaric acid and europium nitrate are placed in comprising n,N-Dimethylformamide, salpeter solution
Mixed solution in reacted, reaction terminate to obtain the final product.
The preparation method of the metal-organic framework functional fluorescence material, specifically includes following steps：With 2- fluorobenzene
Fumaric acid and europium nitrate are placed in the N comprising n,N-Dimethylformamide, nitric acid, N- dimethyl by formic acid as conditioning agent
Formamide solution, water mixed solution in reacted, reaction terminates, by gained mixed solution it is filtered or centrifugation obtain solid
Then precipitation washs solid precipitation with n,N-Dimethylformamide, dichloromethane, last drying.
Preferably, the reaction temperature of the reaction is 100-140 DEG C, reaction time 2-24h.
It is further preferred that the reaction temperature of the reaction is 100-140 DEG C, reaction time 2-24h；The anti-butylene
Molar ratio between diacid, 2- fluobenzoic acids, europium nitrate is (0.02-0.08)：(0.1-0.3)：(0.02-0.05)；The N,
Dinethylformamide, nitric acid N,N-dimethylformamide solution and water between volume ratio be：(1.2-2.4)：(0.05-
0.2)：(0.2-0.8)；A concentration of 1.5-4.5mol/L of the N,N-dimethylformamide solution of the nitric acid.
Metal-organic framework functional fluorescence material of the present invention is in the application in detection probe field.
Preferably, the metal-organic framework functional fluorescence material is in the fluoroscopic examination field of explosive small molecule
Application, the explosive small molecule includes TNP, PNP, 3-NP, 3-NT, 2-NP, 2-NT, 2,6-NT, one kind in 2,4-DNT
It is or a variety of.
The present invention has the following advantages that compared with prior art：
(1) metal-organic framework functional fluorescence material of the present invention, using atom centered on europium, group of the lanthanides gold
Belonging to organic framework material has high-specific surface area, while the fluorescent material of the present invention has excellent fluorescence property again：With color
The features such as damp distinct, fluorescence lifetime is long, larger Stokes shift.In the recognition detection applied to explosive small molecule,
Alternative identification TNP explosive small molecules, it is even more important that there is high sensitivity, to concentration 10-8The explosive of M
Small molecule still has response.
(2) metal-organic framework functional fluorescence material of the present invention, as detection probe, can be recycled.
Description of the drawings
The structure chart of Fig. 1 functional fluorescence material Eu-FUM of the present invention；
Fluorescence intensity figures of Fig. 2 functional fluorescence material Eu-FUM in the DMF solution of different explosive small molecules；
Fig. 3 functional fluorescence materials Eu-FUM immerses the fluorescence intensity figure in various concentration TNP solution；
What is be recycled for multiple times in Fig. 4 functional fluorescence materials Eu-FUM immersion TNP solution is quenched efficiency chart.
Specific embodiment
With reference to embodiments, the present invention is further described in detail, but not limited to this.
Embodiment 1
The metal-organic framework functional fluorescence material prepared in the present embodiment has structural formula：[Eu12(FUM)18]
(H2O)8.Hereinafter referred to as Eu-FUM (similarly hereinafter).
Preparation method is as follows：
Using 2- fluobenzoic acids as conditioning agent, by fumaric acid and europium nitrate be placed in comprising n,N-Dimethylformamide,
It is reacted in the n,N-Dimethylformamide solution of nitric acid and the mixed solution of water, wherein, the fumaric acid dosage is
0.02mmol；The 2- fluobenzoic acids dosage is 0.3mmol；Europium nitrate dosage is 0.02mmol；The N, N- dimethyl formyl
The dosage of amine is 1.2ml；The dosage of salpeter solution be 0.05ml, the n,N-Dimethylformamide solution of the nitric acid it is a concentration of
1.5mol/L；The dosage of water is 0.2ml；Reaction terminates to obtain the final product.
Embodiment 2
The metal-organic framework functional fluorescence material prepared in the present embodiment has structural formula：[Eu12(FUM)18]
(H2O)8。
Preparation method is as follows：
Using 2- fluobenzoic acids as conditioning agent, by fumaric acid and europium nitrate be placed in comprising n,N-Dimethylformamide,
It is reacted in the n,N-Dimethylformamide solution of nitric acid and the mixed solution of water, reaction terminates, and gained mixed solution is passed through
Filtering or centrifugation obtain solid precipitation, and then solid precipitation is washed with n,N-Dimethylformamide, dichloromethane,
Last drying.
Wherein, the fumaric acid dosage is 0.08mmol；The 2- fluobenzoic acids dosage is 0.1mmol；Europium nitrate
Dosage is 0.05mmol；The dosage of the N,N-dimethylformamide is 2.4ml；The dosage of salpeter solution be 0.2ml, the nitre
A concentration of 4.5mol/L of the N,N-dimethylformamide solution of acid；The dosage of water is 0.8ml.
After measured, the duct of the Eu-FUM being prepared is 1D ducts.
Embodiment 3
The metal-organic framework functional fluorescence material prepared in the present embodiment has structural formula：[Eu12(FUM)18]
(H2O)8。
Preparation method is as follows：
Using 2- fluobenzoic acids as conditioning agent, by fumaric acid and europium nitrate be placed in comprising n,N-Dimethylformamide,
It is reacted in the n,N-Dimethylformamide solution of nitric acid and the mixed solution of water, reaction temperature is 100 DEG C, and the reaction time is
2h, reaction terminate, by gained mixed solution it is filtered or centrifugation obtain solid precipitation, then with n,N-Dimethylformamide, two
Chloromethanes washs solid precipitation, last drying.
Wherein, the fumaric acid dosage is 0.08mmol；The 2- fluobenzoic acids dosage is 0.1mmol；Europium nitrate
Dosage is 0.05mmol；The dosage of the N,N-dimethylformamide is 2.4ml；The dosage of salpeter solution be 0.2ml, the nitre
A concentration of 4.5mol/L of the N,N-dimethylformamide solution of acid；The dosage of water is 0.8ml.
After measured, the duct of the Eu-FUM being prepared is 1D ducts.
Embodiment 4
The metal-organic framework functional fluorescence material prepared in the present embodiment has structural formula：[Eu12(FUM)18]
(H2O)8。
Preparation method is as follows：
Using 2- fluobenzoic acids as conditioning agent, by fumaric acid and europium nitrate be placed in comprising n,N-Dimethylformamide,
It is reacted in the n,N-Dimethylformamide solution of nitric acid and the mixed solution of water, reaction temperature is 140 DEG C, and the reaction time is
For 24 hours, reaction terminates, by gained mixed solution it is filtered or centrifugation obtain solid precipitation, then with n,N-Dimethylformamide, two
Chloromethanes washs solid precipitation, last drying.
Wherein, the fumaric acid dosage is 0.08mmol；The 2- fluobenzoic acids dosage is 0.1mmol；Europium nitrate
Dosage is 0.05mmol；The dosage of the N,N-dimethylformamide is 2.4ml；The dosage of salpeter solution be 0.2ml, the nitre
A concentration of 4.5mol/L of the N,N-dimethylformamide solution of acid；The dosage of water is 0.8ml.
Embodiment 5
The metal-organic framework functional fluorescence material prepared in the present embodiment has structural formula：[Eu12(FUM)18]
(H2O)8.The structure chart of functional fluorescence material Eu-FUM as described in Figure 1.
Preparation method is as follows：
By organic ligand fumaric acid (0.06 mM), conditioning agent 2- fluobenzoic acids (0.214 mM) and nitric acid
Europium (0.0413 mM) is in N,N-dimethylformamide (2.2 milliliters), nitric acid (0.1 milliliter of 3.5 mol/L) and water (0.5 milli
Rise) mixed solution in mix, at 120 DEG C heating reaction 6h, be subsequently cooled to room temperature；The white crystal N, N- that will be obtained
The repeated multiple times washing of dimethylformamide, dichloromethane solvent, and room temperature is dried.
Embodiment 6
The material Eu-FUM being prepared in embodiment 1-5 is detected performance test, concrete operation step is such as
Under：
Material Eu-FUM described in 2mg is taken to immerse in the DMF solution containing different explosive small molecules, respectively
0.001mol/L (TNP, PNP, 3-NP, 3-NT, 2-NP, 2-NT, 2,6-NT, 2,4-DNT), and detect its fluorescence intensity.
After measured, the functional fluorescence material Eu-FUM in embodiment 1-5 is in the DMF solution of different explosive small molecules
It is respectively provided with stronger fluorescence intensity；The Eu-FUM that is prepared in embodiment 5 is wherein illustrated in figure 2 in small point of different explosives
Fluorescence intensity figure in the DMF solution of son.
Embodiment 7
The material Eu-FUM being prepared in embodiment 1-5 is detected performance test, concrete operation step is such as
Under：
Material Eu-FUM described in 2mg is taken to immerse in the solution containing various concentration TNP, respectively 10-3,10-4,10-5,10-6,10-7,10-8Mol/L (TNP, PNP, 3-NP, 3-NT, 2-NP, 2-NT, 2,6-NT, 2,4-DNT), and detect its fluorescence intensity.
After measured, the functional fluorescence material Eu-FUM in embodiment 1-5 is respectively provided in various concentration TNP solution is immersed
Stronger fluorescence intensity；It is wherein illustrated in figure 3 the Eu-FUM being prepared in embodiment 5 and is immersing various concentration TNP solution
In fluorescence intensity figure.
Embodiment 8
The material Eu-FUM being prepared in embodiment 1-5 is detected performance test, concrete operation step is such as
Under：
It takes in the TNP solution that material Eu-FUM immersions described in 2mg contain, repeatedly recycles, detect being quenched for its recycling
Efficiency.
After measured, the functional fluorescence material Eu-FUM in embodiment 1-5 still can have after repeatedly TNP solution is immersed
Stronger fluorescence intensity；It is wherein illustrated in figure 4 in the Eu-FUM immersion TNP solution being prepared in embodiment 5 and repeatedly recycles
What is used is quenched efficiency chart.
Obviously, the above embodiments are merely examples for clarifying the description rather than the restriction to embodiment.For
For those of ordinary skill in the art, other various forms of variations or change can also be made on the basis of the above description
It is dynamic.There is no necessity and possibility to exhaust all the enbodiments, and the obvious variation or change thus extended out
Among moving still in the protection domain of the invention.
Claims (8)
1. a kind of metal-organic framework functional fluorescence material, which is characterized in that the structural formula of the fluorescent material is [Eu12
(FUM)18](H2O)8；Each metal europium ion nine of the fluorescent material is coordinated, respectively with the oxygen atom on 6 ligand carboxyls
And 1 moisture sublink, the FUM are fumarate.
2. metal-organic framework functional fluorescence material according to claim 1, which is characterized in that the fluorescent material
Duct be 1D ducts.
3. metal-organic framework functional fluorescence material according to claim 2, which is characterized in that the Europium Metal from
The on-link mode (OLM) of the sub oxygen atom on the ligand carboxyl is linked for an oxygen atom and an europium ion, alternatively, an oxygen
Atom and two europium ion links.
4. a kind of method for preparing the metal-organic framework functional fluorescence material in claim 1-3 described in any one,
It is characterized in that, includes the following steps：Using 2- fluobenzoic acids as conditioning agent, fumaric acid and europium nitrate are placed in comprising N, N-
Dimethylformamide, salpeter solution mixed solution in reacted, reaction terminate to obtain the final product.
5. the preparation method of metal-organic framework functional fluorescence material according to claim 4, which is characterized in that tool
Body includes the following steps：Using 2- fluobenzoic acids as conditioning agent, fumaric acid and europium nitrate are placed in comprising N, N- dimethyl
Formamide, the n,N-Dimethylformamide solution of nitric acid, water mixed solution in reacted, reaction terminates, and gained is mixed
Solution it is filtered or centrifugation obtain solid precipitation, then with n,N-Dimethylformamide, dichloromethane the solid is precipitated into
Row washing, last drying.
6. the preparation method of metal-organic framework functional fluorescence material according to claim 5, which is characterized in that institute
The reaction temperature for stating reaction is 100-140 DEG C, reaction time 2-24h；The fumaric acid, 2- fluobenzoic acids, europium nitrate
Between molar ratio be（0.02-0.08）：（0.1-0.3）：（0.02-0.05）；The N of the N,N-dimethylformamide, nitric acid,
Volume ratio between dinethylformamide solution and water is：（1.2-2.4）：（0.05-0.2）：（0.2-0.8）；The nitric acid
N,N-dimethylformamide solution a concentration of 1.5-4.5mol/L.
7. the metal-organic framework functional fluorescence material in claim 1-3 described in any one is in detection probe field
Using.
8. according to the application described in claim 7, which is characterized in that the metal-organic framework functional fluorescence material
Application in the fluoroscopic examination field of explosive small molecule, the explosive small molecule include TNP, PNP, 3-NP, 3-NT, 2-
It is one or more in NP, 2-NT, 2,6-NT, 2,4-DNT.
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| CN110951084A (en) * | 2018-09-27 | 2020-04-03 | 天津工业大学 | Application of white-light-emitting double-rare-earth metal organic framework material in detection of phenol pollutants |
| CN110951481A (en) * | 2018-09-27 | 2020-04-03 | 天津工业大学 | Application of double rare earth luminescent metal organic framework in phenolic compound detection |
| CN109385751B (en) * | 2018-09-30 | 2021-08-03 | 武汉大学 | Preparation method and application of fluorescent nanofiber membrane based on bimetallic organic framework |
| CN109211863B (en) * | 2018-10-26 | 2021-04-20 | 大连民族大学 | Using Eu2+Method for detecting explosive TNP (trinitrotoluene) by f-f transition spectrum |
| CN110066401B (en) * | 2019-05-16 | 2021-03-02 | 重庆师范大学 | Red fluorescent rare earth europium coordination polymer and preparation method and application thereof |
| CN110174388B (en) * | 2019-06-17 | 2021-10-22 | 重庆理工大学 | Preparation method of detection object for detecting nitrobenzene in solution, detection object and detection method of nitrobenzene concentration |
| CN110387547B (en) * | 2019-08-26 | 2021-04-27 | 中国科学院海洋研究所 | Metal organic framework corrosion inhibitor hydrogel composite material and application thereof |
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