CN108169196B - Method for rapidly detecting fluorine ions in environment - Google Patents
Method for rapidly detecting fluorine ions in environment Download PDFInfo
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- CN108169196B CN108169196B CN201711370833.7A CN201711370833A CN108169196B CN 108169196 B CN108169196 B CN 108169196B CN 201711370833 A CN201711370833 A CN 201711370833A CN 108169196 B CN108169196 B CN 108169196B
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- -1 fluorine ions Chemical class 0.000 title claims abstract description 43
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 33
- 239000011737 fluorine Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000000523 sample Substances 0.000 claims abstract description 40
- 238000000862 absorption spectrum Methods 0.000 claims abstract description 16
- 238000002189 fluorescence spectrum Methods 0.000 claims abstract description 8
- 238000010521 absorption reaction Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000007850 fluorescent dye Substances 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 210000001124 body fluid Anatomy 0.000 claims description 4
- 239000010839 body fluid Substances 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 239000000606 toothpaste Substances 0.000 claims description 4
- 229940034610 toothpaste Drugs 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 238000004445 quantitative analysis Methods 0.000 abstract description 4
- 238000004451 qualitative analysis Methods 0.000 abstract description 2
- 230000004044 response Effects 0.000 abstract description 2
- 238000011897 real-time detection Methods 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- 238000000295 emission spectrum Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229940006461 iodide ion Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 1
- VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
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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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- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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Abstract
The invention discloses a method for rapidly detecting fluorine ions in an environment, and belongs to the technical field of analytical chemistry. Mixing a sample to be detected with a colorimetric probe by adopting an organic solvent; measuring 350nm-600nm ultraviolet absorption spectrum and 400nm-680nm fluorescence emission spectrum; and calculating the concentration of the fluorine ions contained in the sample to be detected according to the measured ultraviolet absorption intensity at 450nm and the fluorescence emission intensity at 555 nm. The method of the invention not only can identify the fluorine ions with high selectivity, but also can carry out quantitative and qualitative analysis on the fluorine ions in a naked eye observation mode. The method realizes quick and effective response to the fluorine ions and realizes real-time detection of the fluorine ions.
Description
Technical Field
The invention relates to a method for rapidly detecting fluorine ions in an environment, in particular to a method for detecting fluorine ions by taking thiazole Schiff bases as a fluorine ion colorimetric fluorescent probe, and belongs to the technical field of analytical chemistry.
Background
Anions are ubiquitous in the environment and in living organisms, such as air, water and soil in the environment, in organs, cells and even cytosol of the human body, and play an extremely important role in the environment and ecosystem. The fluoride ion with the smallest radius in the anion is an essential element for biological life activities and has important functions in the aspects of tooth health care, osteoporosis treatment and the like. In order to be able to contain a sufficient amount of fluoride ions in the human body, it is commonly used as an important additive in toothpastes, medicines and drinking water. However, excessive fluorine not only has toxic effects on aquatic organisms and plants, but also causes serious human health problems. For example, higher concentrations of sodium fluoride (NaF) can interfere with normal cellular metabolism. Acute ingestion of large or long-term low doses of fluorine can lead to acute stomach and renal dysfunction, chronic poisoning of teeth and bones, calculus, and serious even death. Currently, many people still quote water sources containing high fluorine all over the world, which poses a threat to human health.
The research on a method capable of rapidly detecting the existence and the content of the fluorinion has extremely important functions in the aspects of treatment of clinical diseases, environmental protection and academic research. At present, many methods for detecting fluorine ions, such as capillary electrophoresis, nuclear magnetic resonance and the like, unfortunately, the capillary electrophoresis has low sensitivity, the fluorine ion selective electrode has poor reproducibility, and the fluorine ion nuclear magnetic resonance has high cost, so that the application and the development of the method are severely limited. Therefore, the finding of a specific fluoride ion detection and analysis method which is simple in operation, low in cost, high in efficiency and rapid is still an urgent need in the field.
Disclosure of Invention
In order to overcome the defects, the invention provides a method for rapidly and specifically detecting fluorine ions by using a novel fluorine ion colorimetric fluorescent probe. The colorimetric fluorescent probe is simple to operate and low in cost, can even convert a molecular recognition signal into color change, and can be directly carried out with naked eyes without expensive instruments, so that the colorimetric fluorescent probe has remarkable advantages compared with other recognition methods.
Specifically, the invention provides a method for rapidly detecting fluorine ions by using a fluorine ion colorimetric fluorescent probe (thiazole Schiff base compound).
A method for rapidly detecting fluorine ions in an environment is characterized by comprising the following steps:
(a) mixing a sample to be detected with a colorimetric probe in an organic solvent; the structure of the colorimetric fluorescent probe is as follows:
(b) measuring 350nm-600nm ultraviolet absorption spectrum and 400nm-680nm fluorescence emission spectrum;
(c) and calculating the concentration of the fluorine ions contained in the sample to be detected according to the ultraviolet absorption intensity of 450nm and the fluorescence emission intensity of 555 nm.
Further, in the above technical solution, the organic solvent is selected from dimethyl sulfoxide or other solvents that can completely dissolve the sample and the colorimetric probe.
Further, in the above technical solution, the corresponding relationship between the ultraviolet absorption intensity and the fluorescence emission intensity and the concentration of the fluorine ions is determined during the implementation of the method.
Further, in the above technical solution, the correspondence is presented in a standard curve manner.
Further, in the above technical scheme, the sample to be tested is water, soil, food, toothpaste or body fluid. The body fluid may be blood.
The principle of the invention is as follows: the colorimetric fluorescent probe for the fluorinion adopted in the detection method can interact with the fluorinion to generate the change of an ultraviolet absorption spectrum and a fluorescence emission spectrum (simultaneously accompanied with different color changes), thereby realizing the quantitative detection of the fluorinion.
The colorimetric fluorescent probe adopted in the method can generate color reaction after being combined with the fluorine ions, and the concentration of the fluorine ions in the sample to be detected can be determined qualitatively or quantitatively according to the shade of the color. Accordingly, the method of the present invention comprises the steps of:
(a) mixing a sample to be detected with a colorimetric fluorescent probe in an organic solvent; the structure of the colorimetric fluorescent probe is the same as that of the colorimetric fluorescent probe.
(b) Observing the color of the mixed colorimetric fluorescent probe and the sample to be detected;
(c) and qualitatively or quantitatively determining the concentration of the fluorine ions contained in the sample to be detected according to the color intensity.
Further, in the above technical solution, the organic solvent and the sample to be measured are the same as described above.
The colorimetric fluorescent probe for the fluoride ions adopted in the detection method disclosed by the invention can not cause obvious changes of an absorption spectrum and an emission spectrum when respectively acting with other anions, so that the selective identification of the fluoride ions is realized, and further, the colorimetric fluorescent probe can be optionally used for eliminating the interference of the existence of other anions on the quantitative determination of the fluoride ions. Illustratively, the colorimetric fluorescent probes employed in the methods of the invention are directed to chloride ions Cl-Bromine ion Br-Iodide ion I-Hydrogen sulfate ion HSO4 -Nitrate ion NO3 -Dihydrogen phosphate ion H2PO4 -And acetate ion AcO-Neither can lead to significant changes in the absorption spectrum and emission spectrum. Therefore, the method of the invention has strong anti-interference capability.
Advantageous effects of the invention
The colorimetric fluorescent probe for the fluoride ions adopted in the detection method disclosed by the invention can not cause obvious changes of an ultraviolet absorption spectrum and a fluorescence emission spectrum when respectively acting with other anions, so that the selective identification of the fluoride ions is realized, and the interference of the existence of other anions on the quantitative determination of the fluoride ions can be optionally eliminated.
The fluoride ion colorimetric fluorescent probe adopted in the detection method has good stability, and further can be stored and used for a long time.
The method can complete rapid and high-selectivity fluorine ion identification within 5 seconds, and the fluorine ion colorimetric fluorescent probe can also perform qualitative and quantitative analysis in a naked eye observation mode.
The method for detecting the fluorine ions can quickly detect the fluorine ions with high selectivity, is simple to operate and is beneficial to commercial popularization and application.
Drawings
FIG. 1 shows different concentrations F-(0-10. mu.M) effect on the probe (10. mu.M) UV absorption spectrum;
FIG. 2 shows different concentrations F-(0-10. mu.M) effect on fluorescence emission spectra of probes (10. mu.M);
FIG. 3 is a graph showing the effect of different analytes (20. mu.M) on the UV absorption spectrum of a probe (10. mu.M);
FIG. 4 shows the effect of different analytes (20. mu.M) on the fluorescence emission spectra of probes (10. mu.M);
FIG. 5 is a graph showing the quantitative analysis F of the UV absorption spectrum of a probe (10. mu.M) in the presence of different analytes (0. mu.M)-(10. mu.M);
FIG. 6 is a graph showing the quantitative analysis F of the UV absorption spectrum of a probe (10. mu.M) in the presence of different analytes (20. mu.M)-(10. mu.M);
FIG. 7 shows the naked eye detection result of the response of colorimetric fluorescent probe molecules to fluorine ions.
The specific implementation mode is as follows:
the invention will be explained in more detail below by means of the following examples. The following examples are illustrative only, and it should be understood that the present invention is not limited by the following examples.
Example 1
Preparation of colorimetric probes:
185mg (1mmol) of 2-amino-6-chlorobenzothiazole, 232mg (1.2-1.5mmol) of 4- (diethylamino) salicylaldehyde and 3 drops of acetic acid are dissolved in 50m L absolute ethyl alcohol, after heating reflux reaction for 10 hours, the crude product is obtained by reduced pressure filtration, and then the recrystallization is carried out by absolute ethyl alcohol, thus obtaining a light yellow pure product with the yield of 91%.
1HNMR(400MHz,CDCl3):12.64(s,1H),8.93(s,1H),7.79-7.75(m,2H),7.40-7.37(dd,J1＝8.4Hz,J2＝2Hz,1H),7.26-7.24(d,J＝8.4Hz,1H),6.33-6.19(dd,J1＝9.2Hz,J2＝2.4Hz,1H),6.184(s,1H),3.47-3.41(q,J＝7.2Hz,4H),1.26-1.22(t,J＝7.2Hz,6H)；13CNMR(101MHz,CDCl3) 136.22,129.91,127.07,122.66,121.15,108.78,105.64,97.46,45.01, 12.73; ESI-MS calculated 359.9, found 359.9.
Example 2
The test method comprises the following steps: (a) different concentrations of F-(0-10. mu.M) effect on absorption spectra of contrast color fluorescent probes (10. mu.M); (b) different concentrations of F-(0-10. mu.M) influence on emission spectra of contrast color fluorescent probes (10. mu.M). The above assays were performed in dimethylsulfoxide and all spectral measurements were at 25 ℃ F-Measured immediately after addition. The results are shown in FIGS. 1 and 2.
As can be seen from FIG. 1, F is accompanied in the colorimetric fluorescent probe solution-The peak value at 445nm of the absorption spectrum decreases with increasing concentration, while a new peak is generated at 516nm, the intensity increases, and the peak value is between 0 and 10 mu M F-The concentration range and the absorption value form a good linear relationship. As can be seen from FIG. 2, F is accompanied in the colorimetric fluorescent probe solution-The peak value at 500nm of the emission spectrum is reduced when the concentration is increased, a new peak is generated at 555nm, the intensity is increased, and the concentration is 0-10 mu M F-The concentration range and the emission value form a good linear relationship. Therefore, the probe of the invention can accurately determine the content of the fluorine ions in the blood sample or the environment to be detected.
Example 3
Effect of different analytes (20. mu.M) on the ultraviolet absorption spectrum and fluorescence emission of the probe (10. mu.M). The analytes include: fluoride ion F-Chloride ion Cl-Bromine ion Br-Iodide ion I-Sulfur, sulfurAcid hydrogen radical ion HSO4 -Nitrate ion NO3 -Dihydrogen phosphate ion H2PO4 -And acetate ion AcO-Their concentration was 20. mu.M. All test conditions were done in dimethylsulfoxide and all spectra were F at 25 deg.C-Transfer 100 μ L probe stock (1mM) into a 10m L volumetric flask, blow dry, add 9m L dimethyl sulfoxide, transfer 20 μ L the above analyte stock (10mM) into the flask, then add dimethyl sulfoxide to 10m L, shake up, and measure immediately, the results are shown in FIGS. 3 and 4.
As can be seen from fig. 3 and 4, the probe has high selectivity for fluorine ions and can react with fluorine ions in a transfer manner. In the dimethyl sulfoxide solution, compared with other analytes, only after the probe reacts with fluoride ions, the absorption spectrum and the emission spectrum have obvious changes; and the absorption intensity and the emission intensity of other common anions existing in the organism have no obvious change after the action of the other common anions and the probe.
Example 4
The effect of different analytes (20. mu.M) on the probes (10. mu.M) in the UV absorption spectrum and in the fluorescence emission spectrum was quantified for fluoride ions (10. mu.M). The analytes include: fluoride ion F-Chloride ion Cl-Bromine ion Br-Iodide ion I-Hydrogen sulfate ion HSO4 -Nitrate ion NO3 -Dihydrogen phosphate ion H2PO4 -And acetate ion AcO-Their concentration was 20. mu.M. All test conditions were done in dimethylsulfoxide and all spectra were F at 25 deg.C-Transfer 10 μ L probe stock (1mM) into a 10m L volumetric flask, blow dry, add 9m L dimethyl sulfoxide, and transfer 20 μ L of the above analyte stock (10mM) and F-The solution was added to a volumetric flask and then was brought to 10m L with dimethyl sulfoxide, shaken and immediately measured, and the results are shown in FIGS. 5 and 6.
As can be seen from FIGS. 5 and 6, other common anions present in the organism do not significantly interfere with the qualitative and quantitative detection of fluoride ions by the probe, and as can be seen from FIG. 7, the probe can realize rapid naked-eye identification of fluoride ions.
Claims (4)
1. A method for rapidly detecting fluorine ions in an environment is characterized by comprising the following steps:
(a) mixing a sample to be detected with a colorimetric probe in dimethyl sulfoxide; the structure of the colorimetric fluorescent probe is as follows:
(b) measuring 350nm-600nm ultraviolet absorption spectrum and 400nm-680nm fluorescence emission spectrum;
(c) and calculating the concentration of the fluorine ions contained in the sample to be detected according to the ultraviolet absorption intensity of 450nm and the fluorescence emission intensity of 555 nm.
2. The method of claim 1, wherein the method comprises: and determining the corresponding relation between the ultraviolet absorption intensity and the fluorescence emission intensity and the concentration of the fluorine ions in the implementation process of the method.
3. The method of claim 2, wherein the method comprises: the correspondence is presented in a standard curve manner.
4. A method for rapidly detecting fluorine ions in an environment according to color change is characterized by comprising the following steps:
(a) mixing a sample to be detected with a colorimetric fluorescent probe in dimethyl sulfoxide; the structure of the colorimetric fluorescent probe is as follows:
(b) observing the color of the mixed colorimetric fluorescent probe and the sample to be detected;
(c) and qualitatively or quantitatively determining the concentration of the fluorine ions contained in the sample to be detected according to the color intensity.
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| CN105181686A (en) * | 2015-08-27 | 2015-12-23 | 晋江尚京富本环保科技有限公司 | Method for detecting fluoride ions in environment |
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| CN105181686A (en) * | 2015-08-27 | 2015-12-23 | 晋江尚京富本环保科技有限公司 | Method for detecting fluoride ions in environment |
Non-Patent Citations (4)
| Title |
|---|
| An easy prepared dual-channel chemosensor for selective and instant detection of fluoride based on double Schiff-base;Yan-Li Leng 等;《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》;20160527;第167卷;116-121 * |
| Development of multifunctional heterocyclic Schiff base as a potential metal chelator: a comprehensive spectroscopic approach towards drug discovery;Manojkumar Jadhao 等;《J Biol Inorg Chem》;20161107;第22卷;47-59 * |
| Dual-channel detection of Cu2+ and F_ with a simple Schiff-based colorimetric and fluorescent sensor;Yu Jeong Na 等;《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》;20141024;第136卷;1649-1657 * |
| Reversible "OFF–ON" fluorescent and colorimetric sensor based benzothiazole-bisphenol A for fluoride in MeCN;Serkan Erdemir 等;《Sensors and Actuators B》;20150709;第221卷;900-905 * |
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