CN116283771A - Fluorescent compound, application thereof in measuring pH value of solution and pH detection device - Google Patents
Fluorescent compound, application thereof in measuring pH value of solution and pH detection device Download PDFInfo
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 25
- 238000001514 detection method Methods 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 230000002093 peripheral effect Effects 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- ZKONTOQLRAPWED-UHFFFAOYSA-N n-ethylmorpholin-4-amine Chemical compound CCNN1CCOCC1 ZKONTOQLRAPWED-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 10
- 230000007246 mechanism Effects 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 238000004454 trace mineral analysis Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 45
- 230000006872 improvement Effects 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- -1 (2-ethylmorpholino) amino Chemical group 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- 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"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- 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
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Abstract
The invention provides a fluorescent compound, application thereof in measuring the pH value of a solution and a pH detection device, wherein the chemical structural formula of the fluorescent compound is as follows
The compound has a pH response mechanism, can calculate the pH of the solution by detecting the fluorescence intensity value of the solution of the compound, realizes the trace analysis of the pH detection of the solution, and has the advantages of trace, wide pH detection range and high sensitivity.
Description
Technical Field
The invention relates to the field of fluorescent compounds, in particular to a pH-sensitive fluorescent compound, application thereof in measuring the pH value of a solution and a pH detection device.
Background
The pH value is an important index of the pH value of the reaction solution, and the index is widely applied to the production and the life of people. There are many applications in industrial production, both in water treatment processes and in process units in power plants. In addition, the measurement of the pH value of medicines, soil and food has important value in the fields of medicine, agriculture and food detection. Therefore, the method is rapid and has great significance in accurately detecting the pH value of the solution. Currently, the method for detecting the pH value of a solution is mainly a pH meter, and the method requires that an electrode is directly contacted with the solution, so that the required solution quantity is relatively large. Thus, there is a need for a method that can detect the pH of a trace solution without contact.
The fluorescence analysis method is an important micro analysis technology, has the advantages of strong selectivity, short response time, high sensitivity, simple operation and the like, and the method for measuring the pH value of the solution by using the fluorescent compound is a way for micro analysis of the pH value of the solution. At present, the pH value response fluorescent compound is mainly characterized in that the pH value is relatively strong and weak through the change of the fluorescence intensity, and the detection range is generally between 2.0 and 7.0. Fewer probes are available to detect the pH in alkaline environments and quantify the pH. Therefore, a fluorescent probe having a relatively wide pH detection range is required.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art, thereby providing a compound for measuring the pH value of a solution by utilizing a pH response mechanism, and also providing an application of the compound in measuring the pH value of the solution and a pH detection device based on the application.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a fluorescent compound has a chemical structural formula of
The application of the compound in measuring the pH of a solution comprises the steps of adding the fluorescent compound into the solution to be measured, and detecting the fluorescent intensity I of the solution to be measured F Then according to the equation log [ (6242-I) F )/(I F -773.6)]pH of the solution was calculated by =ph-5.45. The compound has a pH response mechanism, and can calculate the pH of the solution by detecting the fluorescence intensity value of the solution of the compound, thereby realizing the trace analysis of the pH detection of the solution. For strong oxidizing solutions, such as concentrated sulfuric acid, potassium permanganate, etc., can react with the compound to oxidize and destroy the structure of the compound, and therefore, the fluorescent compound of the present invention is not suitable for detecting the pH value of the strong oxidizing solution.
As a further improvement of the technical scheme, the pH range of the solution is 3.0-10.0, and the pH deviation of the detection solution is smaller in the range.
As a further improvement of the technical scheme, the compound has high sensitivity, and the concentration of the compound in the solution is 5-15 mu M when the pH of the solution is detected.
As a further improvement of the technical scheme, the concentration of the compound in the solution is 10 μm.
The invention also provides a pH detection device based on the application, which comprises a controller, a radiation light source, an atomizer, a detector, a display and a recorder, wherein the controller comprises a memory and a processor, and is characterized in that the memory comprises a calculation program which can realize the following steps when being executed by the processor: fluorescence intensity I of the solution F Carry-in equation log [ (6242-I) F )/(I F -773.6)]The pH of the solution was calculated in =ph-5.45. The controller, the radiation light source, the atomizer, the detector, the display and the recorder are the components of the existing fluorescence spectrometer, when the specific implementation is carried out, the calculation program can be added into a memory of the existing fluorescence spectrometer, the original fluorescence spectrometer adds fluorescent compounds into the solution to be detected through the addition of the calculation program, and the pH of the solution is measured based on a pH response mechanism of the fluorescent compounds.
The invention also provides a pH detection device based on the application, which comprises a fluorescence spectrometer and a peripheral controller electrically connected with the fluorescence spectrometer, wherein the peripheral controller comprises a memory and a processor, and the fluorescence spectrometer is used for measuring the fluorescence intensity I of a solution F And the fluorescence intensity I F Transmitting to the peripheral controller; the memory includes a computing program which when executed by the processor is capable of performing the steps of: fluorescence intensity I of the solution F Carry-in equation log [ (6242-I) F )/(I F -773.6)]The pH of the solution was calculated in =ph-5.45. The technical scheme is that a controller is added on the basis of an original fluorescence spectrometer, a fluorescent compound is added into a solution to be detected, and then the pH of the solution is measured based on a pH response mechanism of the fluorescent compound.
The preparation method of the fluorescent compound EL comprises the following reaction route
The substituent X of reactant 1 is halogen.
As a further improvement of the technical scheme, in order to increase the availability of the reaction, X in reactant 1 is bromine.
As a further improvement of the technical scheme, in order to balance the cost and the conversion, the ratio of the amount of 4- (2-ethylamino) morpholine to the amount of the substance of reactant 1 at the time of the reaction is 1: (2-4) at 85-95deg.C.
Compared with the prior art, the fluorescent compound has outstanding substantive characteristics and remarkable progress, and particularly, the pH of the solution can be calculated by detecting the fluorescence intensity value of the solution of the compound through a pH response mechanism, so that the trace analysis of the pH detection of the solution can be realized. Further, the compound has a small concentration in the solution and high sensitivity when the pH of the solution is measured. In a further aspect, the fluorescent compounds of the present invention have a broad range of pH values that are detectable based on pH response mechanisms. The fluorescent compound has the advantages of capability of quantitatively testing the pH value of an analysis solution, wide pH value range and high sensitivity.
Drawings
FIG. 1 is an absorption spectrum of EL (10. Mu.M) in different solvents.
FIG. 2 is a graph showing the absorption spectra of EL (10. Mu.M) in B-R buffers of different pH values.
FIG. 3 is a graph showing fluorescence spectra of EL (10. Mu.M) buffer at different pH values B-R.
FIG. 4 is a graph of fluorescence intensity versus pH fit corresponding to 535nm in FIG. 2.
Detailed Description
The technical scheme of the invention is further described in detail through the following specific embodiments.
The materials used in each example were from commercial products. Among them, 4- (2-ethylamino) morpholine and the like are purchased from the technical company of carbofuran. The test instrument of the absorption spectrum is a Hitachi U-2910 spectrophotometer; the fluorescence spectrometer is a Hitachi F-2700 spectrophotometer.
Example 1
Synthesis of organic small molecule fluorescent compound abbreviated as EL
Compound 1 (0.470 g,1 mmol) and 4- (2-ethylamino) morpholine (0.4 mL,3 mmol) were dissolved in 20mL methanol and stirred in the flask for 1h. Reflux at 85℃for 8h after stirringAfter cooling to room temperature, washing with petroleum ether. By CH 2 Cl 2 And CH (CH) 3 OH mixture (CH) 2 Cl 2 And CH (CH) 3 OH with the volume ratio of 10:1-6:1) as eluent, and performing column chromatography separation and purification to obtain 0.46g yellow solid, namely the organic small molecule fluorescent compound, which is chemically named as follows: 4-methyl-N- (2- (6- ((2-ethylmorpholino) amino) -1, 3-dioxo-1H-benzo [ de ]]Isoquinoline-2) ethyl) benzenesulfonamide, abbreviated as EL. And the hydrogen spectrum, the carbon spectrum and the mass spectrum of the compound are characterized, and the structure of the compound is confirmed by analyzing the hydrogen spectrum, the carbon spectrum and the mass spectrum data of the compound. The characterization results are as follows:
1 H NMR(400MHz,CDCl 2 ),δ(ppm):8.45(d,J＝8.0Hz,1H),8.34(d,J＝8.4Hz,1H),8.19(d,J＝7.6Hz,1H),7.66(t,J＝7.8Hz,1H),7.47(d,J＝8.4Hz,2H),6.69-6.74(m,3H),6.49(s,1H),5.32(t,J＝0.8Hz,2H),4.20(t,J＝5.4Hz,2H),3.77(t,J＝4.4Hz,4H),3.37-3.48(m,4H),2.87(s,2H),2.59(s,3H),1.91(s,3H)。 13 C NMR(100MHz,CDCl 2 ),δ(ppm):166.27,165.78,151.25,144.01,138.25,136.00,132.45,131.15,130.44,127.81,126.11,123.87,121.61,110.79,105.82,68.20,57.11,44.41,40.28,40.08,22.12,0.90。
example 2
Photophysical property test experiments of EL in different solvents
Test solutions containing 10. Mu.M EL were prepared with different kinds of organic solvents, and the above solutions were tested for their absorption spectra and fluorescence emission spectra with an ultraviolet spectrophotometer, and the results are shown in FIG. 1.
From FIG. 1, it can be seen that the organic small molecule fluorescent compound has a large absorbance value at 350-500nm, which indicates that the fluorescent compound can be excited in this band.
Example 3
pH response test experiment of EL
The fluorescence emission spectra of the solutions were measured by a fluorescence spectrometer using B-R buffer solutions of different pH values, adding EL, and preparing a test solution containing 10. Mu.MEL. And fitting the fluorescence spectrum to obtain a corresponding curve.
As shown in fig. 2, withThe increase of the pH value causes little change of the fluorescence intensity and displacement of the small organic molecule fluorescent compound, which indicates that the small organic molecule fluorescent compound can be excited by a single excitation wavelength. As can be seen from fig. 3, the fluorescence intensity of the organic small molecule fluorescent compound EL decreases with an increase in pH. Fitting the data of FIG. 3, it can be seen that these data fit to the Henderson-Hasselbalch equation, the equation log [ (6242-I) obtained by fitting F )/(I F
-773.6) ] = pH-5.45, as shown in figure 4. Thus, the pH value of the EL can be obtained by testing the fluorescence intensity of the EL in different solutions.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same; while the invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that the present invention may be modified and equivalents substituted for elements thereof; without departing from the spirit of the invention, it is intended to cover the scope of the invention as claimed.
Claims (10)
1. A fluorescent compound is characterized in that the chemical structural formula is
2. Use of a compound according to claim 1 for measuring the pH of a solution, wherein the fluorescent compound is added to the solution and the fluorescence intensity I of the solution is measured F Then according to the equation log [ (6242-I) F )/(I F -773.6)]pH of the solution was calculated by =ph-5.45.
3. The use according to claim 2, wherein the pH of the detectable solution of the compound is in the range of 3.0 to 9.0.
4. Use according to claim 2, characterized in that the concentration of the compound in solution is 5-15 μm.
5. The use according to claim 2 or 4, wherein the concentration of the compound in solution is 10 μm.
6. A pH testing device for use according to any one of claims 2-5, which is a fluorescence detector, said fluorescence detector comprising a memory and a processor, characterized in that said memory comprises a calculation program, said calculation program being executable by the processor to perform the steps of: fluorescence intensity I of the solution F Carry-in equation log [ (6242-I) F )/(I F -773.6)]The pH of the solution was calculated = pH-5.45.
7. A pH testing device for use according to any one of claims 2-5, comprising a fluorescence spectrometer and a peripheral controller electrically connected to said fluorescence spectrometer, said peripheral controller comprising a memory and a processor, characterized in that said fluorescence spectrometer is adapted to determine the fluorescence intensity I of a solution F And the fluorescence intensity I F Transmitting to the peripheral controller; the memory includes a computing program which when executed by the processor is capable of performing the steps of: fluorescence intensity I of the solution F Carry-in equation ph=log [ (6242-I) F )/(I F -773.6)]The pH of the solution was calculated at +5.45.
8. A process for the preparation of a compound as claimed in claim 1, wherein the reaction scheme is
In the reactant 1, X is halogen.
9. The process of claim 8 wherein X in reactant 1 is bromine.
10. The process according to claim 9, wherein the ratio of the amounts of 4- (2-ethylamino) morpholine to the amount of reactant 1 is 1: (2-4) at 85-95deg.C.
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