CN108484490A - Detect the fluorescence probe and its preparation method and application of various metals ion in water - Google Patents
Detect the fluorescence probe and its preparation method and application of various metals ion in water Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a kind of fluorescence probes and its preparation method and application of various metals ion in detection water.Probe is by Symmetric tetramethyl cucurbituril and anti-4 4（Dimethylamino）1 picoline iodine of styryl is made.Preparation method is to take Tetramethyl melon ring, and Tetramethyl melon ring is dissolved in water, solution A is obtained；Negate 44（Dimethylamino）1 picoline iodine of styryl, by anti-4 4（Dimethylamino）1 picoline iodine of styryl is dissolved in water, and obtains solution B；Solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.Its application is mainly used for detecting caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or the ytterbium ion in water.The probe of the present invention can be detected caesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium different kinds of ions in water, and have the characteristics that higher sensitivity, relatively low testing cost, sample treatment are simple and convenient to operate, measure and quickly and in real time detect.
Description
Technical field
The present invention relates to it is a kind of detection underwater gold category ion fluorescence probe and its preparation method and application, especially one
Kind detection is applied fluorescence probe of caesium in water, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion and preparation method thereof and is answered
With.
Background technology
It is existing currently, caesium in drinking water, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ion detection and analysis mainly pass through
Using absorption/emission spectrum, ion spectra, inductively coupled plasma atomic emission spectrometry and inductively coupled plasma matter
Spectral technology etc..These method accuracy and sensitivity are higher, and still, these detection devices are expensive, and need very professional
Detection technique personnel could complete, testing cost is higher.
And fluorescence probe is a kind of novel detection reagent, since it is with higher sensitivity, relatively low testing cost, sample
The favor that processing is simple and convenient to operate, measures the advantages of quickly and in real time detecting and receive people.But it is now directed at present
The fluorescence probe of underwater gold category ion detection is seldom, and majority is the detection for single metal ion, and simultaneously can be to water
The fluorescence probe that middle caesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ion are detected, has not been reported.
Invention content
The object of the present invention is to provide a kind of fluorescence probes and preparation method thereof of various metals ion in detection water
And application.The probe of the present invention can be detected caesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium different kinds of ions in water, and have
There are higher sensitivity, relatively low testing cost, sample treatment to be simple and convenient to operate, measure the characteristics of quickly and in real time detecting.
Technical scheme of the present invention：The fluorescence probe of various metals ion in a kind of detection water, by symmetrical tetramethyl six
First melon ring is made with trans- 4-4 (dimethylamino) styryl -1- picoline iodine.
The molecular formula of the fluorescence probe of various metals ion in detection water above-mentioned, the probe is C40H44N24O12@
C16H19N2I。
The fluorescence probe of various metals ion in detection water above-mentioned, in the probe Tetramethyl melon ring with it is trans-
The molar ratio of 4-4 (dimethylamino) styryl -1- picoline iodine is 1：0.5-2.
The fluorescence probe of various metals ion in detection water above-mentioned, in the probe Tetramethyl melon ring with it is trans-
The molar ratio of 4-4 (dimethylamino) styryl -1- picoline iodine is 1:1.
A kind of preparation method above-mentioned detecting the fluorescence probe of various metals ion in water, includes the following steps：
1) Tetramethyl melon ring is taken, Tetramethyl melon ring is dissolved in water, solution A is obtained；
2) -4-4 (dimethylamino) styryl -1- picoline iodine is negated, by trans- 4-4 (dimethylamino) styryl -
1- picoline iodine is dissolved in water, and obtains solution B；
3) solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.
In the preparation method of the fluorescence probe of various metals ion in detection water above-mentioned, the step 1) and step 2)
The water of addition is the secondary water of pH=7.
It is a kind of it is above-mentioned detection water in various metals ion fluorescence probe application, be for detect the caesium in water,
Strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion.
The application of the fluorescence probe of various metals ion in detection water above-mentioned, the specific method is as follows：
1) probe is taken, is diluted with water, probe standard solution is obtained；
2) water to be detected is added into probe standard solution made from step 1), places 10-20min, is then swashed with fixed
It sends out wavelength 459nm and carries out fluorescence emission spectrum measurement, and the variation for drawing the fluorescence intensity of the laser wave strong point inspired is bent
Line；
3) fluorescence being added in fluorescence probe solution under water correspondence 582nm to be measured is calculated according to the curve of step 2) to send out
Penetrate spectral intensity changing value Δ F, you can be detected to caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or the ytterbium ion in water.
The application of the fluorescence probe of various metals ion in detection water above-mentioned, in the step 1), probe standard is molten
A concentration of 2.0*10 of liquid-5mol/L。
The application of the fluorescence probe of various metals ion in detection water above-mentioned, it is to be measured when being added in the step 3)
When the variation of fluorescence emission spectrum Strength Changes value Δ F under water correspondence 582nm is more than ± 10%, then show water to be detected
In contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion；When the fluorescence hair being added under water correspondence 582nm to be measured
Penetrate spectral intensity changing value Δ F variation be less than ± 10% when, then show in water to be detected without containing caesium, strontium, barium, iron, chromium,
Mercury, europium, thulium and/or ytterbium ion.
Beneficial effects of the present invention
1, fluorescence probe of the invention can simultaneously to caesium, strontium, barium, iron, chromium, mercury, europium, thulium and ytterbium ion in water simultaneously into
Row detection can detect that there is that detection range is wide as long as wherein containing one or more ions.
2, the present invention is by using Symmetric tetramethyl cucurbituril and trans- 4-4 (dimethylamino) styryl -1- methyl
Pyridine iodine forms super molecular complex, and when detecting above-mentioned metal ion, it is new to be formed that these ions can destroy probe
Compound makes the fluorescence of probe quench again, therefore, can it is simple, quickly, sensitively in water caesium, strontium, barium, iron,
Chromium, mercury, europium, thulium and ytterbium ion are detected.
3, compared with traditional detection method, testing cost substantially reduces the present invention, and operates and be also convenient for, Ke Yishi
When detect.
Interference--free experiments
It prepares respectively and contains alkali metal ion Li+、Na+、K+And Rb+；Alkaline-earth metal Mg2+、Ca2+、Sr2+And Ba2+；Transition gold
Belong to Hg2+、Co2+、Ni2+、Cu2+、Cd2+、Pb2+、Zn2+、Al3+、Fe3+、Fe2+、Y2+、Cr3+And Mn2+；Rare-earth metal La3+、Ce3+、
Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Er3+、Tm3+、Yb3+And Lu3+Solution, above-mentioned ion rubs in solution
Your concentration is 2.0*10-1mol/L。
Above-mentioned solution is separately added into a concentration of 2.0*10-5In the standard solution of the probe of the present invention of mol/L, so
The method according to the invention carries out fluorescence excitation and analysis result afterwards.
Testing result is as shown in Figure 2-5, the experimental results showed that, in aqueous solution, the fluorescence probe of individualism is fixed to swash
Fluorescence intensity level is strong at fluorescence emission wavelengths 582nm when hair wavelength 459nm, slit 5nm, voltage 510v, Cs+,Sr2+,Ba2+,Fe3 +,Cr3+,Hg2+,Eu3+,Tm3+,Yb3+Cs is added in probe standard solution in unstressed configuration spectral quality+,Sr2+,Ba2+,Fe3+,Cr3 +,Hg2+,Eu3+,Tm3+,Yb3+Afterwards, solution fluorescence emission spectrum corresponds to fluorescent emission intensity at 582nm and is substantially reduced, and remaining is golden
Belong to without significant change.The experimental results showed that fluorescence probe is to Cs in alkali metal in alkali metal+There are good selectivity, alkaline earth gold
To Sr in category2+,Ba2+There is good selectivity, Al is removed in transition metal3+Have outside slightly reducing, fluorescence probe is to Hg2+, Fe3 +, Cr3+There is good selectivity.Fluorescence probe is to Eu in rare earth metal3+, Tm3+, Yb3+There is good selectivity.
Quantitative analysis
To a concentration of 2.0*10 produced by the present invention-5Different volumes score is added in the fluorescence probe standard solution of mol/L
Contain Cs+Solution be detected, testing result is as shown in Figure 6, it can be seen that be added different volumes score after standard solution
Middle Cs+Concentration also differ, the Cs of various concentration+Fluorescence probe solution can be made to occur different degrees of quenching, and Cs+Response
The range of linearity be (10.0-70.0) * 10-5Mol/L, detection are limited to 8.24*10-7mol/L。
To a concentration of 2.0*10 produced by the present invention-5Different volumes score is added in the fluorescence probe standard solution of mol/L
Contain Sr2+Or Ba2+Solution be detected, testing result is as Figure 7-8, it can be seen that be added different volumes score after
Sr in standard solution2+Or Ba2+Concentration also differ, the Sr of various concentration2+Or Ba2+Fluorescence probe solution can be made to occur different
The quenching of degree, and Sr2+Or Ba2+The range of linearity of response is (10.0-70.0) * 10-5Mol/L, detection limit are respectively 8.47*
10-7Mol/L and 3.38*10-7mol/L。
To a concentration of 2.0*10 produced by the present invention-5Different volumes score is added in the fluorescence probe standard solution of mol/L
Contain Hg2+、Fe3+Or Cr3+Solution be detected, testing result is as shown in figs. 9-11, it can be seen that be added different volumes
Hg in standard solution after score2+、Fe3+Or Cr3+Concentration also differ, the Hg of various concentration2+、Fe3+Or Cr3+Fluorescence can be made to visit
Different degrees of quenching occurs for needle solution, and Hg2+、Fe3+Or Cr3+The range of linearity of response is (1.0-8.0) * 10-5Mol/L, inspection
Rising limit is respectively 9.18*10-8mol/L、7.35*10-8Mol/L and 8.57*10-8mol/L。
To a concentration of 2.0*10 produced by the present invention-5Different volumes score is added in the fluorescence probe standard solution of mol/L
Contain Eu3+、Tm3+Or Yb3+Solution be detected, testing result is as shown in figs. 12-14, it can be seen that be added different volumes
Eu in standard solution after score3+、Tm3+Or Yb3+Concentration also differ, the Eu of various concentration3+、Tm3+Or Yb3+Fluorescence can be made to visit
Different degrees of quenching occurs for needle solution, and Eu3+、Tm3+Or Yb3+The range of linearity of response is (20.0-140.0) * 10-5mol/
L, detection limit are respectively 1.05*10-6mol/L、1.35*10-6Mol/L and 1.07*10-6mol/L。
Description of the drawings
Attached drawing 1 is the structural schematic diagram of probe of the present invention；
Attached drawing 2 is the fluorescent spectrum curve when solution containing alkali metal ion being added in probe standard solution；
Attached drawing 3 is the fluorescent spectrum curve when solution containing alkaline-earth metal ions being added in probe standard solution；
Attached drawing 4 is the fluorescent spectrum curve when solution containing transition metal ions being added in probe standard solution；
Attached drawing 5 is the fluorescent spectrum curve when solution containing rare metal ion being added in probe standard solution；
Attached drawing 6 is that various concentration is added to contain Cs+Solution when fluorescent spectrum curve；
Attached drawing 7 is that various concentration is added to contain Sr2+Solution when fluorescent spectrum curve；
Attached drawing 8 is that various concentration is added to contain Ba2+Solution when fluorescent spectrum curve；
Attached drawing 9 is that various concentration is added to contain Hg2+Solution when fluorescent spectrum curve；
Attached drawing 10 is that various concentration is added to contain Fe3+Solution when fluorescent spectrum curve；
Attached drawing 11 is that various concentration is added to contain Cr3+Solution when fluorescent spectrum curve；
Attached drawing 12 is that various concentration is added to contain Eu3+Solution when fluorescent spectrum curve；
Attached drawing 13 is that various concentration is added to contain Tm3+Solution when fluorescent spectrum curve；
Attached drawing 14 is that various concentration is added to contain Yb3+Solution when fluorescent spectrum curve.
Specific implementation mode
With reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1：The fluorescence probe of various metals ion in a kind of detection water, by Symmetric tetramethyl cucurbituril with
Trans- 4-4 (dimethylamino) styryl -1- picolines iodine in molar ratio 1：1 is made.
The preparation method of the fluorescence probe of various metals ion in above-mentioned detection water, steps are as follows：
1) Tetramethyl melon ring is taken, Tetramethyl melon ring is added to the secondary water dissolution of pH=7, obtains solution A；
2) -4-4 (dimethylamino) styryl -1- picoline iodine is negated, by trans- 4-4 (dimethylamino) styryl -
1- picoline iodine adds the secondary water dissolution of pH=7, obtains solution B；
3) solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.
The method that above-mentioned fluorescence probe detects caesium in water, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion is as follows：
1) probe is taken, is diluted with water, a concentration of 2.0*10 is produced-5The probe standard solution of mol/L；
2) water to be detected is added into probe standard solution made from step 1), 15min is placed, then to fix excitation wave
Long 459nm carries out fluorescence emission spectrum measurement, and draws the change curve of the fluorescence intensity of the laser wave strong point inspired；
3) fluorescence being added in fluorescence probe solution under water correspondence 582nm to be measured is calculated according to the curve of step 2) to send out
Spectral intensity changing value Δ F is penetrated, when the fluorescence emission spectrum Strength Changes value Δ F's being added under water correspondence 582nm to be measured
When variation is more than ± 10%, then show to contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water to be detected；When adding
When entering the variation of the fluorescence emission spectrum Strength Changes value Δ F under water correspondence 582nm to be measured less than ± 10%, then show to wait for
It detects and does not contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water.
Embodiment 2：The fluorescence probe of various metals ion in a kind of detection water, by Symmetric tetramethyl cucurbituril with
Trans- 4-4 (dimethylamino) styryl -1- picolines iodine in molar ratio 1：0.5 is made.
The preparation method of the fluorescence probe of various metals ion in above-mentioned detection water, steps are as follows：
1) Tetramethyl melon ring is taken, Tetramethyl melon ring is added to the secondary water dissolution of pH=7, obtains solution A；
2) -4-4 (dimethylamino) styryl -1- picoline iodine is negated, by trans- 4-4 (dimethylamino) styryl -
1- picoline iodine adds the secondary water dissolution of pH=7, obtains solution B；
3) solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.
The method that above-mentioned fluorescence probe detects caesium in water, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion is as follows：
1) probe is taken, is diluted with water, a concentration of 2.0*10 is produced-5The probe standard solution of mol/L；
2) water to be detected is added into probe standard solution made from step 1), 10min is placed, then to fix excitation wave
Long 459nm carries out fluorescence emission spectrum measurement, and draws the change curve of the fluorescence intensity of the laser wave strong point inspired；
3) fluorescence being added in fluorescence probe solution under water correspondence 582nm to be measured is calculated according to the curve of step 2) to send out
Spectral intensity changing value Δ F is penetrated, when the fluorescence emission spectrum Strength Changes value Δ F's being added under water correspondence 582nm to be measured
When variation is more than ± 10%, then show to contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water to be detected；When adding
When entering the variation of the fluorescence emission spectrum Strength Changes value Δ F under water correspondence 582nm to be measured less than ± 10%, then show to wait for
It detects and does not contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water.
Embodiment 3：The fluorescence probe of various metals ion in a kind of detection water, by Symmetric tetramethyl cucurbituril with
Trans- 4-4 (dimethylamino) styryl -1- picolines iodine in molar ratio 1：2 are made.
The preparation method of the fluorescence probe of various metals ion in above-mentioned detection water, steps are as follows：
1) Tetramethyl melon ring is taken, Tetramethyl melon ring is added to the secondary water dissolution of pH=7, obtains solution A；
2) -4-4 (dimethylamino) styryl -1- picoline iodine is negated, by trans- 4-4 (dimethylamino) styryl -
1- picoline iodine adds the secondary water dissolution of pH=7, obtains solution B；
3) solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.
The method that above-mentioned fluorescence probe detects caesium in water, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion is as follows：
1) probe is taken, is diluted with water, a concentration of 2.0*10 is produced-5The probe standard solution of mol/L；
2) water to be detected is added into probe standard solution made from step 1), 20min is placed, then to fix excitation wave
Long 459nm carries out fluorescence emission spectrum measurement, and draws the change curve of the fluorescence intensity of the laser wave strong point inspired；
3) fluorescence being added in fluorescence probe solution under water correspondence 582nm to be measured is calculated according to the curve of step 2) to send out
Spectral intensity changing value Δ F is penetrated, when the fluorescence emission spectrum Strength Changes value Δ F's being added under water correspondence 582nm to be measured
When variation is more than ± 10%, then show to contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water to be detected；When adding
When entering the variation of the fluorescence emission spectrum Strength Changes value Δ F under water correspondence 582nm to be measured less than ± 10%, then show to wait for
It detects and does not contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water.
Claims (10)
1. the fluorescence probe of various metals ion in a kind of detection water, it is characterised in that：By Symmetric tetramethyl cucurbituril with
Trans- 4-4（Dimethylamino）Styryl -1- picoline iodine is made.
2. the fluorescence probe of various metals ion in detection water according to claim 1, it is characterised in that：The probe
Molecular formula be C40H44N24O12@C16H19N2I。
3. the fluorescence probe of various metals ion in detection water according to claim 1, it is characterised in that：The probe
Middle Tetramethyl melon ring and trans- 4-4（Dimethylamino）The molar ratio of styryl -1- picoline iodine is 1：0.5-2.
4. the fluorescence probe of various metals ion in detection water according to claim 3, it is characterised in that：The probe
Middle Tetramethyl melon ring and trans- 4-4（Dimethylamino）The molar ratio of styryl -1- picoline iodine is 1：1.
5. a kind of preparation side for detecting the fluorescence probe of various metals ion in water according to claim 1-4 any one of them
Method, which is characterized in that include the following steps：
1）Tetramethyl melon ring is taken, Tetramethyl melon ring is dissolved in water, solution A is obtained；
2）Negate -4-4（Dimethylamino）Styryl -1- picoline iodine, by trans- 4-4（Dimethylamino）Styryl -1- first
Yl pyridines iodine is dissolved in water, and obtains solution B；
3）Solution A and solution B are mixed, reaction at normal temperatures can be prepared by probe.
6. the preparation method of the fluorescence probe of various metals ion, feature exist in detection water according to claim 5
In：The step 1）With step 2）The water of middle addition is the secondary water of pH=7.
7. a kind of application detecting the fluorescence probe of various metals ion in water according to claim 1-4 any one of them,
It is characterized in that：It is for detecting the caesium in water, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion.
8. the application of the fluorescence probe of various metals ion in detection water according to claim 7, which is characterized in that tool
Body method is as follows：
1）The probe is taken, is diluted with water, probe standard solution is obtained；
2）To step 1）Water to be detected is added in probe standard solution obtained, 10-20min is placed, then to fix excitation wave
Long 459nm carries out fluorescence emission spectrum measurement, and draws the change curve of the fluorescence intensity of the laser wave strong point inspired；
3）According to step 2）Curve calculate fluorescence probe solution in the fluorescence emission under water correspondence 582nm to be measured is added
Spectral intensity changing value Δ F, you can caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or the ytterbium ion in water are detected.
9. the application of the fluorescence probe of various metals ion in detection water according to claim 8, it is characterised in that：Institute
State step 1）In, a concentration of 2.0*10 of probe standard solution-5mol/L。
10. the application of the fluorescence probe of various metals ion in detection water according to claim 8, it is characterised in that：
The step 3）In, when the variation for the fluorescence emission spectrum Strength Changes value Δ F being added under water correspondence 582nm to be measured is more than
When ± 10%, then show to contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion in water to be detected；Before water to be measured is added
When corresponding to the variation of the fluorescence emission spectrum Strength Changes value Δ F under 582nm afterwards less than ± 10%, then show in water to be detected not
Contain caesium, strontium, barium, iron, chromium, mercury, europium, thulium and/or ytterbium ion.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109652062A (en) * | 2018-12-25 | 2019-04-19 | 贵州大学 | A kind of novel fluorescence probe T and its preparation and application |
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| CN110208235A (en) * | 2019-06-26 | 2019-09-06 | 贵州大学 | The fluorescence probe and its detection method of pesticide dodine in a kind of detection water |
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| CN113670867A (en) * | 2021-07-16 | 2021-11-19 | 贵州大学 | Supermolecule fluorescence sensing array and method for detecting multiple metal ions in aqueous solution |
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| CN109580564B (en) * | 2018-11-28 | 2021-04-13 | 贵州大学 | Method for detecting mercury ions in water |
| CN109608472B (en) * | 2018-12-12 | 2021-04-06 | 贵州大学 | Water-soluble supramolecular fluorescent probe and preparation and application thereof |
| CN109608472A (en) * | 2018-12-12 | 2019-04-12 | 贵州大学 | A kind of water solubility supermolecule fluorescence probe and its preparation and application |
| CN109652062A (en) * | 2018-12-25 | 2019-04-19 | 贵州大学 | A kind of novel fluorescence probe T and its preparation and application |
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| CN110208235A (en) * | 2019-06-26 | 2019-09-06 | 贵州大学 | The fluorescence probe and its detection method of pesticide dodine in a kind of detection water |
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| CN110412000A (en) * | 2019-07-31 | 2019-11-05 | 贵州大学 | Fluorescence probe and its detection method based on ten yuan of melon ring detection L-Trps |
| CN110412000B (en) * | 2019-07-31 | 2022-05-17 | 贵州大学 | Fluorescent probe for detecting L-tryptophan based on ten-element cucurbituril and detection method thereof |
| CN113670867A (en) * | 2021-07-16 | 2021-11-19 | 贵州大学 | Supermolecule fluorescence sensing array and method for detecting multiple metal ions in aqueous solution |
| CN114292642A (en) * | 2021-12-03 | 2022-04-08 | 黔南民族医学高等专科学校 | Preparation and application of six-membered cucurbituril-levofloxacin carbon quantum dot fluorescent probe |
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