CN110240707A - Rear modified metal-organic framework material and the preparation method and application thereof of one kind detection iron ion - Google Patents
Rear modified metal-organic framework material and the preparation method and application thereof of one kind detection iron ion Download PDFInfo
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Abstract
The invention discloses rear modified metal-organic framework materials and the preparation method and application thereof of a kind of detection iron ion.The metal-organic framework materials are with metal ion Tb3+Metal-organic framework materials Tb-HIA is made by hydro-thermal method, and modify and obtain after being carried out with acryloyl chloride to Tb-HIA, the chemical formula of the metal-organic framework materials Tb-HIA are as follows: [M using 5- Hydroxy M Phthalic Acid as organic linking ligand for nodem(L)n·(H2O)q(NO3)], in formula, L is 5- Hydroxy M Phthalic Acid, and M is metal ion Tb3+；M, n and q is respectively the number of metal ion, organic linking ligand and hydrone, wherein m=1, n=1, q=5.Material provided by the invention has the detection of ferric ion highly selective, can be used as the fluorescence probe for detecting ferric ion；Preparation process of the invention is simple, environmental-friendly, at low cost, is easy to large scale preparation.
Description
Technical field
The present invention relates to metal-organic framework materials fields, and in particular to the rear modified metal-of one kind detection iron ion has
Machine framework material and the preparation method and application thereof.
Background technique
Iron is one of element needed by human, and as metal generally existing in cell, iron has the function of various cells
Important role, such as RNA and DNA synthesis in electronics transfer and oxygen metabolism.But in human body iron excess and shortage
It will lead to various biological disorders, such as heredity pigmentation disease, cirrhosis, anaemia, only the iron ability of normal contents
Guarantee human health.So development iron ion probe material effectively, highly sensitive and with specificity is clinically and physiology
Medically there is important directive significance.
However, design synthesizes with highly selective, high sensitivity and can efficiently identify the detection technique of iron ion
It is at present being still the project of a great challenge.By the unremitting effort of scientific worker, formd atomic absorption method,
The detection method of the tradition iron ion such as polarography, potassium dichromate method, volumetric method, spectrophotometry, but it was found that above this
Methods often exist complicated for operation a bit, and sensitivity is low, the deficiencies of cannot detecting to trace iron.In order to realize to Fe3+Ion
High sensitivity, selectivity and accuracy detection, many be based on fluorescence and colorimetric detection Fe3+Method be established.But mesh
The fluorescence probe material of the iron ion identification of the preceding overwhelming majority will be really applied in real production and living, and scientific worker also needs
It solves the problems, such as follows:
1. reported part probe material is often limited to other heavy metal ion, such as Cu2+, Al3+And Cr3+Deng to knowledge
The interference of other process, design and easy preparation specificity are very urgent to the probe of iron ion, are of great significance；
2. most of Small-molecule probe may be only available for organic solvent system or organic/water mixed system, cannot be applicable in
In pure aquatic system, therefore exploitation can detect the probe of iron ion in pure aquatic system and need to be mentioned in current research
It is high；
3. most of highly selective iron ion probe mechanism of action is not yet fully apparent from now.
Summary of the invention
An object of the present invention is to provide rear modified metal-organic framework material of a kind of detection iron ion, and price is just
It preferably, can specificity detection iron ion.
The second object of the present invention is to provide a kind of system of rear modified metal-organic framework material of above-mentioned detection iron ion
Preparation Method, simple process can be mass-produced.
One of to achieve the above object, the technical solution adopted by the present invention is that: the rear modified metal-of one kind detection iron ion
Organic framework material, with metal ion Tb3+For node, with 5- Hydroxy M Phthalic Acid (H2HIA it is) organic linking ligand, passes through
An example metal-organic framework materials Tb-HIA is made in hydro-thermal method, and modifies after being carried out with acryloyl chloride to Tb-HIA, obtains three-dimensional
Metal-organic framework materials Tb-HIAAC；
Its reaction formula is as follows:
Tb3++H2HIA→Tb-HIA
The chemical formula of the metal-organic framework materials Tb-HIA are as follows: [Mm(L)n·(H2O)q(NO3)], in formula,
L is organic linking ligand H2HIA, 5- Hydroxy M Phthalic Acid, structural formula are shown in formula I；
M is metal ion Tb3+；
M, n and q is respectively the number of metal ion, organic linking ligand and hydrone, wherein m=1, n=1, q=5.
To achieve the above object two, the technical solution adopted by the present invention is that: a kind of rear modified metal-detecting iron ion
The preparation method of organic framework material, includes the following steps:
S1, the soluble-salt for weighing 5- Hydroxy M Phthalic Acid and terbium respectively according to molar ratio 1:1.4~1.6, are placed in
In glass sample bottle, water is added and makees solvent, adding sodium hydroxide regulation system pH is 8~9, and is stirred evenly；
S2, glass sample bottle is placed in hydrothermal synthesis reaction kettle, under the conditions of 110~112 DEG C insulation reaction 72~
75h；
S3, to after reaction, cooling obtains colourless bulk crystals, then is successively filtered, washed, dries in air
Processing, obtains metal-organic framework materials Tb-HIA；
S4, acryloyl chloride is added dropwise into the anhydrous methylene chloride solution of Tb-HIA, triethylamine tune is added dropwise after all dripping off again
Section system pH is 8~9, is stirred at room temperature and stays overnight, after reaction, obtains colourless product；Filtering, washing, and in air
Middle drying obtains metal-organic framework materials Tb-HIAAC.
Preferably, the 5- Hydroxy M Phthalic Acid, terbium soluble-salt molar ratio be 1:1.5.
Preferably, the soluble-salt of the terbium is terbium nitrate hexahydrate.
Preferably, in step S4, the Tb-HIA, acryloyl chloride mass volume ratio be 54:0.05g/mL.
Preferably, in step S3, wash conditions are to be washed with water, and are washed 3~5 times.
Preferably, in step S4, wash conditions are to be washed with methylene chloride, are washed 3~5 times.
The chemical equation for preparing Tb-HIAAC is as follows:
The third object of the present invention is to provide a kind of answering for rear modified metal-organic framework material of above-mentioned detection iron ion
With.
Metal-organic framework materials provided by the invention can be used as fluorescence probe, be applied in specificity detection aqueous solution
Ferric ion.
Because metal-organic framework (Metal-organic Frameworks, MOFs) material is by metal ion and organic
Connector is formed by coordinate bond self assembly, is easy to introduce fluorescent functional by metal ion, ligand or guest molecule etc..
The scope of design that there is double carboxylic acid groups iron ion identification material is expanded for the ligand of coordination site rich in hydroxyl is used, with
Terbium ion obtains an example metal-organic framework materials by a step hydro-thermal reaction, and with acryloyl chloride to the gold for being rich in hydroxyl
Category-organic framework material is modified after carrying out, and obtains the organic bone of metal-that an example has the three-dimensional of acrylate group, macropore
Frame material, the material can be stabilized in aqueous solution, and have the fluorescence emission peak based on rare earth ion, not only can be real
Existing metal-organic framework materials in the form of fluorescent quenching to the detection of iron ion, and include alkali metal, alkaline-earth metal,
The specificity to iron ion detection is embodied in transition metal and other heavy metal ion.
The starting material that the present invention uses is cheap, environmental-friendly, and the ligand used can close by simple method
At and yield it is higher, chemical property is stablized, and preparation process is simple, at low cost, is easy to large scale preparation.
Detailed description of the invention
Fig. 1 is the structure chart of metal-organic framework materials Tb-HIA prepared by the embodiment of the present invention 1；
Fig. 2 is the structure chart of metal-organic framework materials Tb-HIAAC prepared by the embodiment of the present invention 2；
Fig. 3 is fluorescence titration of the metal-organic framework materials of the preparation of the embodiment of the present invention 2 to iron ion detection process
Figure；
Fig. 4 is choice experiment histogram of the metal-organic framework materials to iron ion of the preparation of the embodiment of the present invention 2；
Fig. 5 is that metal-organic framework materials prepared by the embodiment of the present invention 2 scheme the PXRD of iron ion detection mechanism；
Fig. 6 is infrared spectroscopy of the metal-organic framework materials to iron ion detection mechanism of the preparation of the embodiment of the present invention 2
Figure.
Specific embodiment
The present invention is further described in the following with reference to the drawings and specific embodiments.
Raw materials and reagents used in following embodiment are unless otherwise specified conventional commercial commodity.
Embodiment 1: the synthesis of metal-organic framework materials Tb-HIA
Weigh 5.5mg 5- Hydroxy M Phthalic Acid (H2HIA) (0.03mmol), 20mg Tb (NO3)3·6H2O
(0.045mmol) in the glass sample bottle of 10mL, be added 2mL water make solvent, add sodium hydroxide regulation system pH be 8~
9, then glass sample bottle is placed in hydrothermal synthesis reaction kettle, then hydrothermal synthesis reaction kettle is placed in electric drying oven with forced convection
In, 110 DEG C of constant temperature, 72h is reacted, after reaction, cooling obtains colourless bulk crystals, and it is collected by filtration, is washed with water 3~5 times,
And dry in air, metal-organic framework materials Tb-HIA, yield: 94% is made.C8H14NO13Tb:C 19.56%, H
2.87%, O 42.35%；Found:C 19.57%, H 2.90%, O 42.33%.Structure as shown in Figure 1,5- hydroxyl isophthalic
The 1 dimension chain that dioctyl phthalate and Tb are formed passes through nitrate anion and π ..., and pi accumulation acts on forming 2 layer structures.
Embodiment 2: the synthesis of metal-organic framework materials Tb-HIAAC
54mg Tb-HIA is added in the anhydrous methylene chloride of 5mL, it is (pure that 0.05mL acryloyl chloride is then added dropwise thereto
96%), after all dripping off it is 8~9 that triethylamine regulation system pH is added dropwise in degree again, by resulting mixture in room temperature after all dripping off
Lower stirring is simultaneously stayed overnight, and after reaction, obtains colourless product.It is collected by filtration, is washed 3~5 times with methylene chloride, and in air
It is dry, metal-organic framework materials Tb-HIAAC, yield 75% is made.Structure is as shown in Figure 2, it can be seen that the top Tb-HIA
The structure for dividing hydroxyl to be modified by chloroacetic chloride.
To the test experience of iron ion
The material Tb-HIAAC in embodiment 2 is weighed, the standard suspension of the water of 0.20mM is configured to, takes 3mL above-mentioned outstanding
Turbid is in quartz colorimetric utensil, then the iron ion Fe of 0.02M is successively added dropwise thereto3+Aqueous solution, until fluorescence intensity is no longer sent out
It changes and turns to only, amounting to and iron concentration is added is 0.2mM, excitation wavelength 305nm, record it respectively in 491nm, 545nm,
The fluorescence emission peak of 586nm and 622nm.The results are shown in attached figure 3, it can be seen that with iron ion Fe3+The increase Tb-HIAAC of concentration
Fluorescence generation be significantly quenched, the degree of being quenched reaches 98%.
Selectivity experiment to iron ion
In selectivity test experiment, takes probe standard suspension 3mL into quartz colorimetric utensil, other ion (Ag are added+,
Li+,Na+,K+,Ca2+,Ba2+,Sr2+,Mg2+,Mn2+,Cd2+,Co2+,Hg2+,Fe2+,Ni2+,Al3+,Cr3+,Zn2+,Cu2+,Pb2+)
0.2mM excites at 305nm, tests its fluorescence intensity change, using species of metal ion as abscissa, relative intensity of fluorescence is
Ordinate obtains selective figure.Then the iron ion Fe of 0.2mM is added into above-mentioned solution again3+Solution, equally in 305nm
Place excitation, test its fluorescence intensity change, obtain competitive assay figure, as a result as shown in fig. 4, it can be seen that other selections sun from
Son is to Fe3+Detection do not influence, show Tb-HIAAC to Fe3+The specificity that has had of detection.
Research to iron ion detection mechanism
The material 5mg in 2 parts of embodiments 2 is weighed, the iron ion Fe of 0.3mM is added in portion3+Solution, stirring 5 minutes, in addition
Portion is not handled, and is filtered, and filter cake carries out PXRD test and infrared spectroscopy (IR) test.As a result respectively as shown in attached drawing 5,6.From figure
There are several new peaks compared to primary sample in the 5 PXRD spectrograms that can be seen that the sample of Tb-HIAAC absorption iron ion, say
It is bright to there are new species to generate, but its integral skeleton structure is to maintain；As seen in Figure 6, compared to Tb-
HIAAC, the stretching vibration peak for adsorbing C=O in the infrared spectrum of iron ion have occurred apparent red shift, show C=O and iron ion
Coordination has occurred, comprehensive PXRD and IR spectrogram shows that Tb-HIAAC is since Tb-HIAAC passes through to the detection of iron ion
Coordination has occurred in carbonyl and iron ion.
Embodiment 3: the synthesis of metal-organic framework materials Tb-HIAAC
Weigh 5.5mg 5- Hydroxy M Phthalic Acid (H2HIA) (0.03mmol), 19mg Tb (NO3)3·6H2O
(0.042mmol) in the glass sample bottle of 10mL, be added 2mL water make solvent, add sodium hydroxide regulation system pH be 8~
9, then glass sample bottle is placed in hydrothermal synthesis reaction kettle, then hydrothermal synthesis reaction kettle is placed in electric drying oven with forced convection
In, 110 DEG C of constant temperature, 72h is reacted, after reaction, cooling obtains colourless bulk crystals, and it is collected by filtration, is washed with water 3~5 times,
And dry in air, metal-organic framework materials Tb-HIA is made, yield: 90%, structure is the same as embodiment 1.
54mg Tb-HIA is added in the anhydrous methylene chloride of 5mL, it is (pure that 0.05mL acryloyl chloride is then added dropwise thereto
Triethylamine regulation system pH is added dropwise in degree again after 96%) all dripping off be 8~9, by resulting mixture in room temperature after all dripping off
Lower stirring is simultaneously stayed overnight, and after reaction, obtains colourless product.It is collected by filtration, is washed 3~5 times with methylene chloride, and in air
It is dry, metal-organic framework materials Tb-HIAAC is made, yield 73%, structure is the same as embodiment 2.
Embodiment 4: the synthesis of metal-organic framework materials Tb-HIAAC
Weigh 5.5mg 5- Hydroxy M Phthalic Acid (H2HIA) (0.03mmol), 21.7mg Tb (NO3)3·6H2O
(0.048mmol) in the glass sample bottle of 10mL, be added 2mL water make solvent, add sodium hydroxide regulation system pH be 8~
9, then glass sample bottle is placed in hydrothermal synthesis reaction kettle, then hydrothermal synthesis reaction kettle is placed in electric drying oven with forced convection
In, 112 DEG C of constant temperature, 75h is reacted, after reaction, cooling obtains colourless bulk crystals, and it is collected by filtration, is washed with water 3~5 times,
And dry in air, metal-organic framework materials Tb-HIA is made, yield: 91%, structure is the same as embodiment 1.
54mg Tb-HIA is added in the anhydrous methylene chloride of 5mL, it is (pure that 0.05mL acryloyl chloride is then added dropwise thereto
96%), after all dripping off it is 8~9 that triethylamine regulation system pH is added dropwise in degree again, by resulting mixture in room temperature after all dripping off
Lower stirring is simultaneously stayed overnight, and after reaction, obtains colourless product.It is collected by filtration, is washed 3~5 times with methylene chloride, and in air
It is dry, metal-organic framework materials Tb-HIAAC is made, yield 76%, structure is the same as embodiment 2.
Claims (8)
1. rear modified metal-organic framework material of one kind detection iron ion, which is characterized in that with metal ion Tb3+For node,
Using 5- Hydroxy M Phthalic Acid as organic linking ligand, metal-organic framework materials Tb-HIA is made by hydro-thermal method, and with third
Alkene acyl chlorides is modified after carrying out to Tb-HIA and is made；The chemical formula of the metal-organic framework materials Tb-HIA are as follows: [Mm(L)n·
(H2O)q(NO3)], in formula, L is 5- Hydroxy M Phthalic Acid, and M is metal ion Tb3+；M, n and q be respectively metal ion, it is organic
The number of linking ligand and hydrone, wherein m=1, n=1, q=5.
2. a kind of preparation method of rear modified metal-organic framework material of a kind of detection iron ion described in claim 1,
It is characterized in that, includes the following steps:
S1, the soluble-salt for weighing 5- Hydroxy M Phthalic Acid and terbium respectively according to molar ratio 1:1.4~1.6, are placed in glass
In sample bottle, water is added and makees solvent, adding sodium hydroxide regulation system pH is 8~9, and is stirred evenly；
S2, glass sample bottle is placed in hydrothermal synthesis reaction kettle, 72~75h of insulation reaction under the conditions of 110~112 DEG C；
S3, to after reaction, cooling obtains colourless bulk crystals, then at being successively filtered, washed, drying in air
Reason, obtains metal-organic framework materials Tb-HIA；
S4, acryloyl chloride is added dropwise into the anhydrous methylene chloride solution of Tb-HIA, triethylamine is added dropwise after all dripping off again and adjusts body
Be pH be 8~9, be stirred at room temperature and overnight, after reaction, obtain colourless product；Filtering, washing, and do in air
It is dry, obtain metal-organic framework materials Tb-HIAAC.
3. the preparation method of rear modified metal-organic framework material of a kind of detection iron ion according to claim 2,
Be characterized in that, in step S1, the 5- Hydroxy M Phthalic Acid, terbium soluble-salt molar ratio be 1:1.5.
4. the preparation side of rear modified metal-organic framework material of a kind of detection iron ion according to claim 2 or 3
Method, which is characterized in that the soluble-salt of the terbium is terbium nitrate hexahydrate.
5. the preparation method of rear modified metal-organic framework material of a kind of detection iron ion according to claim 2,
Be characterized in that, in step S4, the Tb-HIA, acryloyl chloride mass volume ratio be 54:0.05g/mL.
6. the preparation method of rear modified metal-organic framework material of a kind of detection iron ion according to claim 2,
It is characterized in that, in step S3, wash conditions are to be washed with water, and are washed 3~5 times.
7. the preparation method of rear modified metal-organic framework material of a kind of detection iron ion according to claim 2,
It is characterized in that, in step S4, wash conditions are to be washed with methylene chloride, are washed 3~5 times.
8. rear modified metal-organic framework material of a kind of detection iron ion described in claim 1 is being examined as fluorescence probe
Survey the application in aqueous solution in terms of ferric ion.
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| CN116589689A (en) * | 2023-02-14 | 2023-08-15 | 山西大学 | Three-dimensional binuclear terbium coordination polymer and preparation method and application thereof |
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