CN109880623A - A kind of water sensitive upconverting fluorescent material and preparation method thereof and detection method - Google Patents
A kind of water sensitive upconverting fluorescent material and preparation method thereof and detection method Download PDFInfo
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Abstract
The invention discloses a kind of water sensitive upconverting fluorescent material and preparation method thereof and detection methods.The water sensitive upconverting fluorescent material is the surface-functionalized rare earth up-conversion fluorescent material PEI-NaBiF of water-soluble polyethyleneimine4:Yb3+/Er3+It uses solvent-thermal method to prepare, process is as follows: bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine are dissolved in ethylene glycol, then it is reacted 6-24 hours at 180-210 DEG C in water heating kettle, after reaction, reaction solution is centrifuged, washs, being dried to obtain the water sensitive upconverting fluorescent material.A kind of method that the method for the present invention establishes novel measurement Water in Organic Solvents content, using surface-functionalized upconverting fluorescent material (PEI-NaBiF4:Yb3+/Er3+) it is fluorescence probe, degree difference is extinguished to up-conversion fluorescence using different water contents and realizes measurement, the features such as the method has measurement range wide, and background interference is small, and detection is easy.
Description
Technical field
The invention belongs to Water in Organic Solvents assay technical field, in particular to a kind of water sensitive up-conversion fluorescence material
Material and preparation method thereof and detection method.
Background technique
Water has a very important significance life as one of most important physical resources.With the hair of science and technology
Exhibition, micro water are typically considered the impurity in dry products, Food Inspection, environment measuring and some chemical products, therefore
The method that Water in Organic Solvents content can be quickly and effectively detected attracts wide attention.
There are many detections that method can be used for water content at present, such as: Karl_Fischer method, coulomb method, dew point method etc..But
Be that these instrument detection methods have the following deficiencies: (1) instrumentation used in is complicated, expensive, should not promote;(2) multiple
Miscellaneous sample pre-treatments;(3) technical professional.Therefore, a kind of new method for measuring water content in organic solvent is invented
It has very important significance.
Rare earth up-conversion fluorescent material NaBiF4:Yb3+/ Er3+Its excitation wavelength is located at infrared region, launch wavelength position
In visibility region, thus relative to common fluorescent material have many advantages, such as background interference it is small, selectivity good, high sensitivity.Therefore
Rare earth up-conversion has been widely used for fluorescence detection.In addition, due to its good biocompatibility, up-conversion fluorescence material
Material has also been applied to the fields such as bio-imaging.Currently, utilizing the upconverting fluorescent material NaBiF of water sensitive4:Yb3+/Er3+With
It yet there are no any open report in the measurement of Water in Organic Solvents content.
By retrieval, patent publication us related with the present patent application is not yet found.
Summary of the invention
It is glimmering the purpose of the present invention is to provide being converted in a kind of water sensitive for above-mentioned technical problem of the existing technology
Luminescent material and preparation method thereof and detection method.
Using the application in up-conversion fluorescence probe in organic solvent water content detection, this method utilizes organic the present invention
Water content difference causes up-conversion fluorescence to extinguish degree difference in solvent, thus realize the measurement to water content, method operation letter
Single, wide to determination of moisture range, background interference is few, detection is easy.
A kind of water sensitive upconverting fluorescent material, it is characterised in that it is water-soluble polyethyleneimine surface work
The rare earth up-conversion fluorescent material PEI-NaBiF of energyization4:Yb3+/Er3+。
The preparation method of a kind of water sensitive upconverting fluorescent material, it is characterised in that prepared using solvent-thermal method
PEI-NaBiF4:Yb3+/Er3+, process is as follows: bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine are molten
Then solution is reacted 6-24 hours at 180-210 DEG C, after reaction, reaction solution is through being centrifuged in ethylene glycol in water heating kettle
It separates, wash, being dried to obtain the water sensitive upconverting fluorescent material.
The preparation method of a kind of water sensitive upconverting fluorescent material, it is characterised in that bismuth nitrate, erbium nitrate, nitric acid
The molar ratio of ytterbium, sodium nitrate and ammonium fluoride is 75-80:1-3:15-25:180-220:750-850.
The preparation method of a kind of water sensitive upconverting fluorescent material, it is characterised in that bismuth nitrate and polyethyleneimine
Mass ratio be 3.5-4:1-2, the ratio between quality of bismuth nitrate and the volume of ethylene glycol are 3-5:100-300, and the unit of quality is
G, the unit of volume are mL.
Utilize the detection method of the water sensitive upconverting fluorescent material, it is characterised in that the following steps are included:
1) it makes standard curve: organic solvent is mixed with water, uniform intervals prepare water content in the organic solution of 0-100%;Have
The water sensitive upconverting fluorescent material is added in machine solution, after room temperature reaction 0.5-1.5 minutes, in the laser of 980 nm wavelength
Under irradiation, the emission spectrum of the organic solution of different moisture content is measured with Fluorescence Spectrometer, obtains the fluorescence intensity at 540 nm
With the working curve of water content, equation of linear regression I=aC+b is obtained through fitting, C is water content, and I is fluorescence intensity;
2) measure water content: the water sensitive upconverting fluorescent material is added in sample to be tested, the solvent of sample to be tested with
The organic solvent of step 1) is identical, after room temperature reaction 0.5-1.5 minutes, under the laser irradiation of 980 nm wavelength, with fluorescence light
Spectrometer measures the emission spectrum of sample to be tested, obtains the fluorescence intensity at 540 nm, is updated to step 1) equation of linear regression, i.e.,
The water content in sample to be tested can be calculated.
Utilize the detection method of the water sensitive upconverting fluorescent material, it is characterised in that in step 1), organic solvent
For at least one of ethyl alcohol, N,N-dimethylformamide, methanol, acetone.
Utilize the detection method of the water sensitive upconverting fluorescent material, it is characterised in that in step 1), in water sensitive
Concentration of the conversion luminescent material in the organic solution is 10-25 mg/mL;Step 2 water sensitive upconverting fluorescent material exists
Concentration in sample to be tested is identical as concentration of the step 1) water sensitive upconverting fluorescent material in the organic solution.
Utilize the detection method of the water sensitive upconverting fluorescent material, it is characterised in that in step 2, sample to be tested
Water content be 0-100%.
Compared with the existing technology, the beneficial effect that the present invention obtains is:
1, the rare earth upconversion nano fluorescent material PEI-NaBiF that the present invention uses4:Yb3+/Er3+The high, light with luminous intensity
The high characteristic of chemical stabilization.Upconverting fluorescent material PEI-NaBiF prepared by the present invention4:Yb3+/Er3+It is soluble in ethyl alcohol etc.
In organic solvent.
2, the water-soluble rare earth upconversion nano fluorescent material synthetic method that the present invention utilizes is simple.
3, a kind of method that the method for the present invention establishes novel measurement Water in Organic Solvents content, use are surface-functionalized
Upconverting fluorescent material (PEI-UCNPs) be fluorescence probe, it is different to extinguish degree to up-conversion fluorescence using different water contents
Realize measurement, the method has measurement range wide, and background interference is small, detects the features such as easy.
Detailed description of the invention
Launching light spectrogram of the water content from the 11 uniform intervals concentration of 0%-100% in Fig. 1 ethanol solution;
In the ethyl alcohol of Fig. 2 fitting at water content and 540 nm fluorescence intensity working curve;
Launching light spectrogram of the water content from the 11 uniform intervals concentration of 0%-100% in Fig. 3 N, N- dimethyl formyl solution;
The N of Fig. 4 fitting, in N- dimethyl formyl at water content and 540 nm fluorescence intensity working curve;
Launching light spectrogram of the water content from the 11 uniform intervals concentration of 0%-100% in Fig. 5 methanol solution;
In the methanol of Fig. 6 fitting at water content and 540 nm fluorescence intensity working curve;
Launching light spectrogram of the water content from the 11 uniform intervals concentration of 0%-100% in Fig. 7 acetone soln;
In the acetone of Fig. 8 fitting at water content and 540 nm fluorescence intensity working curve.
Specific embodiment
The present invention is further explained in the light of specific embodiments, but the scope of protection of the present invention is not limited thereto.
Embodiment 1:
Utilize the surface-functionalized upper conversion nano fluorescent material PEI- of the water-soluble polyethyleneimine of solvent structure
NaBiF4:Yb3+/Er3+, synthesizing reagent used in this material is bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and gathers
Aziridine.Wherein, the quality of bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine is respectively
0.3824 g, 0.008923 g, 0.09183 g, 0.1590 g, 0.3060 g and 0.1450 g.Dissolve them in 25 mL second
In glycol, reacted 8 hours in water heating kettle with 200 DEG C, after reaction, reaction solution is centrifuged, washs, is dried to obtain
State upconverting fluorescent material.
A certain amount of above-mentioned upconverting fluorescent material is added in the ethanol solution of different water contents, in ethanol solution on
The concentration of conversion luminescent material is about 15 mg/mL.After reacting 1 minute at room temperature, with the Infrared irradiation of 980 nm of excitation wavelength
Ethanol solution measures the emission spectrum of the ethanol solution of different moisture content with Fluorescence Spectrometer, as shown in Figure 1.
Working curve is drawn: using water content as abscissa, the fluorescence intensity at 540 nm is ordinate mapping, through being fitted
It is water content to equation of linear regression I=916846.82-8629.99C, C, I is fluorescence intensity, as a result sees Fig. 2.The result shows that:
When water content is between 0-100%, good linear relationship, R are presented between fluorescence intensity at 540 nm wavelength2=
0.9634, it can be used as working curve for measuring water content in ethyl alcohol.
The simulation ethanol solution that water content is 1% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (simulation is added
The concentration of upconverting fluorescent material is about 15 mg/mL in ethanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates ethanol solution, and the fluorescence intensity at actually measured 540 nm is 909980, asks according to working curve
Obtaining water content is 0.8%.
The simulation ethanol solution that water content is 50% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (mould is added
The concentration of upconverting fluorescent material is about 15 mg/mL in quasi- ethanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates ethanol solution, and the fluorescence intensity at actually measured 540 nm is 463580, asks according to working curve
Obtaining water content is 52.5%.
The simulation ethanol solution that water content is 96% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (mould is added
The concentration of upconverting fluorescent material is about 15 mg/mL in quasi- ethanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates ethanol solution, and the fluorescence intensity at actually measured 540 nm is 89676, acquires according to working curve
Water content is 95.8%.
Embodiment 2:
Utilize the surface-functionalized rare earth upconversion nano fluorescent material PEI- of the water-soluble polyethyleneimine of solvent structure
NaBiF4:Yb3+/Er3+, synthesizing reagent used in this material is bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and gathers
Aziridine.Wherein, the quality of bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine is respectively
0.3695 g, 0.008996 g, 0.08854 g, 0.1716 g, 0.2750 g and 0.1180 g.Dissolve them in 20 mL second
In glycol, reacted 10 hours in water heating kettle with 210 DEG C, after reaction, reaction solution is centrifuged, washs, is dried to obtain
Above-mentioned upconverting fluorescent material.
A certain amount of above-mentioned upconverting fluorescent material is added in the n,N-Dimethylformamide solution of different water contents,
The concentration of upconverting fluorescent material is about 10 mg/mL in N,N-dimethylformamide solution.At room temperature react 1 minute after, with swash
The Infrared irradiation n,N-Dimethylformamide solution for sending out 980 nm of wavelength, the N of different moisture content, N- are measured with Fluorescence Spectrometer
The emission spectrum of dimethyl formamide solution, as shown in Figure 3.
Working curve is drawn: using water content as abscissa, the fluorescence intensity at 540 nm is ordinate mapping, through being fitted
It is water content to equation of linear regression I=901121.82-7959.20C, C, I is fluorescence intensity, as a result sees Fig. 4.The result shows that:
When water content is between 0-100%, good linear relationship, R are presented between fluorescence intensity at 540 nm wavelength2=
0.9738, it can be used as working curve for measuring water content in n,N-Dimethylformamide.
The simulation n,N-Dimethylformamide solution that water content is 3% is prepared in simulation, and a certain amount of above-mentioned upper conversion is added
Fluorescent material (concentration of upconverting fluorescent material is about 10 mg/mL in simulation n,N-Dimethylformamide solution), at room temperature instead
After answering 1 minute, n,N-Dimethylformamide solution, actually measured 540 nm are simulated with the Infrared irradiation of 980 nm of excitation wavelength
The fluorescence intensity at place is 874310, and acquiring water content according to working curve is 3.4%.
The simulation n,N-Dimethylformamide solution that water content is 50% is prepared in simulation, and a certain amount of above-mentioned upper conversion is added
Fluorescent material (concentration of upconverting fluorescent material is about 10 mg/mL in simulation n,N-Dimethylformamide solution), at room temperature instead
After answering 1 minute, n,N-Dimethylformamide solution, actually measured 540 nm are simulated with the Infrared irradiation of 980 nm of excitation wavelength
The fluorescence intensity at place is 523740, and acquiring water content according to working curve is 47.4%.
The simulation n,N-Dimethylformamide solution that water content is 90% is prepared in simulation, and a certain amount of above-mentioned upper conversion is added
Fluorescent material (concentration of upconverting fluorescent material is about 10 mg/mL in simulation n,N-Dimethylformamide solution), at room temperature instead
After answering 1 minute, n,N-Dimethylformamide solution, actually measured 540 nm are simulated with the Infrared irradiation of 980 nm of excitation wavelength
The fluorescence intensity at place is 196420, and acquiring water content according to working curve is 88.5%.
Embodiment 3:
Utilize the surface-functionalized rare earth upconversion nano fluorescent material PEI- of the water-soluble polyethyleneimine of solvent structure
NaBiF4:Yb3+/Er3+, synthesizing reagent used in this material is bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and gathers
Aziridine, wherein bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine quality be respectively
0.3715 g, 0.008972 g, 0.08884 g, 0.1685 g, 0.3590g and 0.1600g.Dissolve them in 20 mL second two
In alcohol, reacted 9 hours in water heating kettle with 205 DEG C, after reaction, reaction solution is centrifuged, washs, it is above-mentioned to be dried to obtain
Upconverting fluorescent material.
A certain amount of above-mentioned upconverting fluorescent material is added in the methanol solution of different water contents, in methanol solution on
The concentration of conversion luminescent material is about 20 mg/mL.After reacting 1 minute at room temperature, with the Infrared irradiation of 980 nm of excitation wavelength
Methanol solution measures the emission spectrum of the methanol solution of different moisture content with Fluorescence Spectrometer, as shown in Figure 5.
Working curve is drawn: using water content as abscissa, the fluorescence intensity at 540 nm is ordinate mapping, through being fitted
It is water content to equation of linear regression I=978725.64-10921.27C, C, I is fluorescence intensity, as a result sees Fig. 6.The result shows that:
When water content is between 0-100%, good linear relationship, R are presented between fluorescence intensity at 540 nm wavelength2=
0.9633, it can be used as working curve for measuring the analysis of water content in methanol.
The simulation methanol solution that water content is 2% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (simulation is added
The concentration of upconverting fluorescent material is about 20 mg/mL in methanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates methanol solution, and the fluorescence intensity at actually measured 540 nm is 953440, asks according to working curve
Obtaining water content is 2.3%.
The simulation methanol solution that water content is 50% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (mould is added
The concentration of upconverting fluorescent material is about 20 mg/mL in quasi- methanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates methanol solution, and the fluorescence intensity at actually measured 540 nm is 456750, asks according to working curve
Obtaining water content is 47.8%.
The simulation methanol solution that water content is 90% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (mould is added
The concentration of upconverting fluorescent material is about 20 mg/mL in quasi- methanol solution), after reacting 1 minute at room temperature, with excitation wavelength 980
The Infrared irradiation of nm simulates methanol solution, and the fluorescence intensity at actually measured 540 nm is 3040, acquires according to working curve
Water content is 89.3%.
Embodiment 4:
Utilize the surface-functionalized rare earth upconversion nano fluorescent material PEI- of the water-soluble polyethyleneimine of solvent structure
NaBiF4:Yb3+/Er3+, synthesizing reagent used in this material is bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and gathers
Aziridine, wherein bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and polyethyleneimine quality be respectively
0.3923 g, 0.008798 g, 0.09024 g, 0.1730 g, 0.3124 g and 0.1300 g.Dissolve them in 30 mL second
In glycol, reacted 11 hours in water heating kettle with 190 DEG C, after reaction, reaction solution is centrifuged, washs, is dried to obtain
Above-mentioned upconverting fluorescent material.
A certain amount of above-mentioned upconverting fluorescent material is added in the acetone soln of different water contents, in acetone soln on
The concentration of conversion luminescent material is about 25 mg/mL.After reacting 1 minute at room temperature, with the Infrared irradiation of 980 nm of excitation wavelength
Acetone soln measures the emission spectrum of the acetone soln of different moisture content with Fluorescence Spectrometer, as shown in Figure 7.
Working curve is drawn: using water content as abscissa, the fluorescence intensity at 540 nm is ordinate mapping, through being fitted
It is water content to equation of linear regression I=827344.12-7363.82C, C, I is fluorescence intensity, as a result sees Fig. 8.The result shows that:
When water content is between 0-100%, good linear relationship, R are presented between fluorescence intensity at 540 nm wavelength2=
0.9872, it can be used as working curve for measuring the analysis of water content in acetone.
The acetone soln that water content is 5% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (simulation acetone is added
The concentration of upconverting fluorescent material is about 25 mg/mL in solution), after reacting 1 minute at room temperature, with 980 nm's of excitation wavelength
Infrared irradiation solution, the fluorescence intensity at actually measured 540 nm are 785240, and acquiring water content according to working curve is
5.7%。
The acetone soln that water content is 50% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (simulation third is added
The concentration of upconverting fluorescent material is about 25 mg/mL in ketone solution), after reacting 1 minute at room temperature, with 980 nm of excitation wavelength
Infrared irradiation solution, the fluorescence intensity at actually measured 540 nm is 473881, and acquiring water content according to working curve is
48.0%。
The acetone soln that water content is 92% is prepared in simulation, and a certain amount of above-mentioned upconverting fluorescent material (simulation third is added
The concentration of upconverting fluorescent material is about 25 mg/mL in ketone solution), after reacting 1 minute at room temperature, with 980 nm of excitation wavelength
Infrared irradiation solution, the fluorescence intensity at actually measured 540 nm is 159800, and acquiring water content according to working curve is
90.6%。
In terms of the detection data of embodiment 1 ~ 4, method detection water content of the invention and actual value only have minimum deviation,
Detection accuracy is higher, and when carrying out detection water content, sample to be tested is not required to carry out special preprocessing process.Through the invention
Method can detect the water content in different organic solvents.
Content described in this specification is only to enumerate to inventive concept way of realization, and protection scope of the present invention is not answered
When the concrete form for being seen as limited by embodiment and being stated.
Claims (8)
1. a kind of water sensitive upconverting fluorescent material, it is characterised in that it is surface-functionalized dilute of water-soluble polyethyleneimine
Native upconverting fluorescent material PEI-NaBiF4:Yb3+/Er3+。
2. a kind of preparation method of water sensitive upconverting fluorescent material according to claim 1, it is characterised in that using molten
Agent thermal method prepares PEI-NaBiF4:Yb3+/Er3+, process is as follows: bismuth nitrate, erbium nitrate, ytterbium nitrate, sodium nitrate, ammonium fluoride and poly-
Aziridine is dissolved in ethylene glycol, then reacts 6-24 hours at 180-210 DEG C in water heating kettle, after reaction, instead
It answers liquid to be centrifuged, wash, being dried to obtain the water sensitive upconverting fluorescent material.
3. a kind of preparation method of water sensitive upconverting fluorescent material according to claim 2, it is characterised in that bismuth nitrate,
Erbium nitrate, ytterbium nitrate, sodium nitrate and ammonium fluoride molar ratio be 75-80:1-3:15-25:180-220:750-850.
4. a kind of preparation method of water sensitive upconverting fluorescent material according to claim 2, it is characterised in that bismuth nitrate
Mass ratio with polyethyleneimine is 3.5-4:1-2, and the ratio between quality and the volume of ethylene glycol of bismuth nitrate are 3-5:100-300,
The unit of quality is g, and the unit of volume is mL.
5. a kind of detection method using water sensitive upconverting fluorescent material described in claim 1, it is characterised in that including with
Lower step:
1) it makes standard curve: organic solvent is mixed with water, uniform intervals prepare water content in the organic solution of 0-100%;Have
The water sensitive upconverting fluorescent material is added in machine solution, after room temperature reaction 0.5-1.5 minutes, in the laser of 980 nm wavelength
Under irradiation, the emission spectrum of the organic solution of different moisture content is measured with Fluorescence Spectrometer, obtains the fluorescence intensity at 540 nm
With the working curve of water content, equation of linear regression I=aC+b is obtained through fitting, C is water content, and I is fluorescence intensity;
2) measure water content: the water sensitive upconverting fluorescent material is added in sample to be tested, the solvent of sample to be tested with
The organic solvent of step 1) is identical, after room temperature reaction 0.5-1.5 minutes, under the laser irradiation of 980 nm wavelength, with fluorescence light
Spectrometer measures the emission spectrum of sample to be tested, obtains the fluorescence intensity at 540 nm, is updated to step 1) equation of linear regression, i.e.,
The water content in sample to be tested can be calculated.
6. detection method according to claim 4, it is characterised in that in step 1), organic solvent is ethyl alcohol, N, N- diformazan
At least one of base formamide, methanol, acetone.
7. detection method according to claim 4, it is characterised in that in step 1), water sensitive upconverting fluorescent material exists
Concentration in the organic solution is 10-25 mg/mL;Step 2 water sensitive upconverting fluorescent material is dense in sample to be tested
It spends identical as concentration of the step 1) water sensitive upconverting fluorescent material in the organic solution.
8. detection method according to claim 4, it is characterised in that in step 2, the water content of sample to be tested is 0-
100%。
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WO2021164242A1 (en) * | 2020-02-18 | 2021-08-26 | 同济大学 | Method for utilizing fluorescent material to express changes in humidity of bonding mortar |
CN112649605A (en) * | 2020-12-14 | 2021-04-13 | 哈尔滨理工大学 | Based on NaBiF4ECL biosensor of up-conversion nano-particles |
CN113122237A (en) * | 2021-04-20 | 2021-07-16 | 中国计量大学上虞高等研究院有限公司 | Infrared probe material and preparation method and application thereof |
CN113122237B (en) * | 2021-04-20 | 2022-05-24 | 中国计量大学上虞高等研究院有限公司 | Infrared probe material and preparation method and application thereof |
CN115651633A (en) * | 2022-09-27 | 2023-01-31 | 中国科学院宁波材料技术与工程研究所 | X-ray fluorescence excitation imaging contrast agent and preparation method and application thereof |
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