CN115141152B - Fluorescent reagent for detecting water content in organic solvent, preparation method and detection method thereof - Google Patents
Fluorescent reagent for detecting water content in organic solvent, preparation method and detection method thereof Download PDFInfo
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Abstract
The invention discloses a fluorescent reagent for detecting the water content in an organic solvent, a preparation method and a detection method thereof, wherein the fluorescent reagent is a neutral red derivative, and the corresponding chemical structural formula is as follows:
. The invention also specifically discloses a preparation method of the fluorescent reagent and a method for detecting the water content in the organic solvent. The preparation method of the reagent is simple, the reagent detects the water content in the proton type organic solvent and the aprotic type organic solvent through fluorescence change or solution color change, the reagent and the research thereof lay a theoretical basis for the detection and application of the water in the organic solvent, and a new thought and method are provided for novel water sensing.
Description
Technical Field
The invention belongs to the technical field of organic molecular fluorescent reagents, and particularly relates to a fluorescent reagent for detecting the water content in an organic solvent, a preparation method and a detection method thereof.
Background
Water is a common impurity in organic solvents, and the reaction rate and yield can be influenced by water contained in the organic solvents, so that the experimental process of the organic synthesis can be greatly influenced. For example: in organic synthesis experiments, some reactions need to be carried out in completely anhydrous conditions, otherwise the reactions are affected and even more serious results are caused, so that the detection of the water content in an organic solvent is an important task. In the medical field, trace amounts of water in the medicament may lead to reduced efficacy and even to unwanted side effects of the medicament; the cleaning of integrated circuit boards typically uses high purity organic solvents and trace amounts of water can affect the performance of the circuit board. Currently, the determination of the water content in an organic reagent generally adopts a traditional karl-fischer titration method, but the determination method has some disadvantages, such as complex operation process and use of toxic pyridine reagent.
In recent years, fluorescent reagents have been widely focused by researchers due to their high efficiency, sensitivity, real-time performance, and the like. So far, little research is done on the application of the reagent to water detection in organic solvents, and development of a novel fluorescent reagent for detecting the water content in organic solvents and a method for rapidly and effectively determining the water content in organic solvents are urgently needed.
Disclosure of Invention
The invention solves the technical problem of providing a fluorescent reagent for detecting the water content in an organic solvent, a preparation method and a detection method thereof, and the fluorescent reagent can be used for rapidly and effectively determining the water content in the organic solvent.
The invention adopts the following technical scheme to solve the technical problems, and is a fluorescent reagent for detecting the water content in an organic solvent, which is characterized in that: the fluorescent reagent is a neutral red derivative, and the corresponding chemical structural formula is as follows:
the invention relates to a preparation method of a fluorescent reagent for detecting the water content in an organic solvent, which is characterized by comprising the following specific steps: adding a surfactant solution and a neutral red solution into a colorimetric tube, mixing, standing for reaction for two days, and generating a black substance in the colorimetric tube, wherein the black substance is a neutral red derivative, and the surfactant is sodium dodecyl sulfate.
Further defined, the concentration of sodium dodecyl sulfate in the surfactant solution and the concentration of neutral red in the neutral red solution are both 0.1mol/L, and the volume ratio of the surfactant solution to the neutral red solution is 1:1.
The invention relates to a method for detecting the water content in an organic solvent by using a fluorescent reagent, which is characterized by comprising the following specific steps: when the detection environment is methanol, the neutral red derivative emits orange fluorescence in pure methanol, the fluorescence is weakened to emit orange fluorescence in the presence of water, and the fluorescent indicator can be used for detecting water in methanol; in a titration test of water, along with the addition of water, the fluorescence intensity is reduced sharply, a linear relation exists between the water content and the fluorescence intensity, and the fluorescence indicator can be used for detecting the water content in methanol; when the detection environment is ethanol, the neutral red derivative emits orange fluorescence in the pure ethanol, the fluorescence peak intensity changes under the condition that trace water exists, the fluorescence intensity is reduced along with the addition of water, and the fluorescence indicator can be used for detecting water in the ethanol; in a titration test of water, with the addition of water, there is a linear relationship between water content and fluorescence intensity, and the fluorescent indicator can be used for detecting the water content in ethanol; when the detection condition is acetone, the color of the aqueous solution changes when a small amount of the aqueous solution is added, and the fluorescent indicator can be used for detecting the water content in the acetone by a colorimetric method.
Based on the experimental results, the fluorescent indicators for detecting water in methanol, ethanol and acetone can be proved to be novel fluorescent sensing molecules with high sensitivity. Because the neutral red derivative is sensitive to the external environment, and the water has strong polarity, as the water is added, the neutral red derivative molecules and the water molecules form hydrogen bonds, so that the molecules are twisted to form a TICT state, and the fluorescence peak position is red shifted and the fluorescence is weakened or quenched.
Compared with the prior art, the invention has the following advantages and beneficial effects: the preparation method of the reagent is simple, the reagent detects the water content in the proton type organic solvent and the aprotic type organic solvent through fluorescence change or solution color change, the reagent and the research thereof lay a theoretical basis for the detection and application of the water in the organic solvent, and a new thought and method are provided for novel water sensing.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a neutral red derivative;
FIG. 2 is an infrared plot of neutral red derivatives;
FIG. 3 is a graph showing fluorescence spectra in a water/methanol mixture containing 0-90% water content of neutral red derivative;
FIG. 4 is a plot of fluorescence peak intensity of neutral red derivatives as a function of water content in methanol (v/v%);
FIG. 5 is a graph of fluorescence spectra in water/ethanol mixtures of neutral red derivative reagents 0% -100% water content;
FIG. 6 is a graph of fluorescence spectra in water/ethanol mixtures of neutral red derivatives 4% -20% water content;
FIG. 7 is a graph showing the color change of a neutral red derivative 0% -90% water/methanol mixture under 365nm ultraviolet light;
FIG. 8 is a graph showing the color change of a neutral red derivative 0% -100% water/ethanol mixture under 365nm ultraviolet light;
FIG. 9 is a graph showing the color change of neutral red derivatives in a mixture of acetone and water under natural light;
FIG. 10 is a graph showing the color change of neutral red derivatives in acetone/water mixtures under 365nm ultraviolet light.
Detailed Description
The above-described matters of the present invention will be described in further detail by way of examples, but it should not be construed that the scope of the above-described subject matter of the present invention is limited to the following examples, and all techniques realized based on the above-described matters of the present invention are within the scope of the present invention.
Example 1
A preparation method of a fluorescent reagent for detecting the water content in an organic solvent comprises the following steps: preparing neutral red solution and sodium dodecyl sulfonate solution with the concentration of 0.1mol/L, adding the neutral red solution and the sodium dodecyl sulfonate solution into a colorimetric tube according to the volume ratio of 1:1, standing for two days to react completely, washing and centrifuging the materials which are black and insoluble in water in the colorimetric tube with high-purity water, repeating the steps for 4 to 5 times, putting the materials into a baking oven, setting the temperature to 60 ℃ for 48 hours, and putting the materials into a centrifuge tube for sealing and storing after the neutral red derivatives are dried. The hydrogen spectrogram 1 is shown in the infrared figure 2. 1 H NMR (600 MHz, DMSO) δ 7.92 (d, J = 9.6 Hz, 1H), 7.78 (s, 1H), 7.52 (dd, J = 9.6, 2.7 Hz, 1H), 6.87 (s, 1H), 6.74 (s, 1H), 3.37 (d, J = 48.7 Hz, 25H), 3.24 (s, 6H), 2.33 (s, 3H)。
Example 2
In methanol solvent, neutral red derivative reagent in methanol with increasing water addition.
10mg of neutral red derivative is weighed in a 10mL volumetric flask, and dichloromethane is added to dissolve and fix the volume to the scale, so as to prepare 1mg/mL of liquid to be detected. And adding 50 mu L of the liquid to be detected into a 10mL colorimetric tube to prepare methanol/water solutions with different concentrations, wherein the color of the solution is changed from yellow to red, and the water volume percentage content is respectively 0%,2%,5%,10%,20%,30%,50%,70%,80% and 90% in the range, so that the fluorescent property of the liquid is tested. The change of the fluorescence spectrum and fluorescence intensity of neutral red derivative/methanol with increasing water content is shown in fig. 3 and 4. FIG. 3 is a fluorescence emission image of a water/methanol solution of neutral red derivative water content with excitation wavelength of 463nm. It can be seen from the graph that with the addition of water, the fluorescence gradually quenched and the emission peak position gradually red shifted, and that there was a good linear relationship between the water content by volume percentage of 2% -50%, and fig. 7 illustrates that with the addition of water, the fluorescence color changed from orange yellow to no fluorescence color under 365nm ultraviolet light, indicating that the fluorescent reagent was a quenched fluorescent reagent when water was detected.
Example 3
In methanol solvent, neutral red derivatives increase the fluorescence peak intensity with water content as a function of linear fit to the water content in methanol (v/v%).
The neutral red derivative prepared in example 1 was taken out, fluorescence-dissolved in methylene chloride to prepare a stock solution of 1mg/mL, 50. Mu.L of the stock solution was taken out and added to a 10mL cuvette, and 0mL, 0.2mL, 0.5mL, 1.0mL, 2.0mL, 5.0mL, 1.0mL, 2.0mL, 3.0mL and 5.0mL of deionized water were respectively added to the 10mL cuvette to prepare a methanol/water solution of 2%,5%,10%,20%,30% and 50% by volume, and the fluorescence properties were measured. FIG. 4 is a plot of fluorescence peak intensity as water content increases versus water content in methanol (v/v%). As shown in fig. 3 and 4, as the water content in methanol increases from 2% to 100%, the fluorescence intensity gradually decreases and the fluorescence color changes from orange to orange, and as the water content in methanol is in the range of 2% to 50% by volume, there is a linear relationship between the water content and the fluorescence intensity, and the correlation coefficient R 2 = 0.9966, the detection limit is 0.265%, the detection range is 2% -50%, and the method can be used for quantitative detection of water in methanol.
Example 4
10mg of neutral red derivative is weighed in a 10mL volumetric flask, and dichloromethane is added to dissolve and fix the volume to the scale, so as to prepare 1mg/mL of liquid to be detected. And adding 50 mu L of the liquid to be detected into a 10mL colorimetric tube to prepare ethanol/water solutions with different concentrations, wherein the volume percentage of water in the range is 0%,2%,5%,10%,20%,30%,50%,70%,80%,90%,100% respectively, and testing the fluorescence properties of the liquid. The change in fluorescence intensity of neutral red derivative/ethanol with increasing water content is shown in FIG. 5. As can be seen from fig. 5, as the water content in ethanol increases, the fluorescence peak intensity starts to decrease, and the position of the fluorescence emission peak gradually red-shifts. As can be seen in FIG. 8, with the addition of water, the fluorescence color changed from orange to red to no fluorescence under 365nm ultraviolet light, indicating that the addition of water resulted in fluorescence quenching and the water content in ethanol was detected.
Example 5
In ethanol solvent, neutral red derivatives increased the linear fit function of fluorescence peak intensity with water content (v/v%) in ethanol.
The neutral red derivative prepared in example 1 was dissolved in methylene chloride to prepare a stock solution of 1mg/mL, 50. Mu.L of the stock solution was taken out and added to a 10mL cuvette, and 0mL, 0.2mL, 0.5mL, 1.0mL, 2.0mL, 3.0mL, 5.0mL, 7.0mL and 8.0mL of deionized water were added to the 10mL cuvette to prepare ethanol/water solutions of 0%,2%,5%,10%,20%,30%,50%,70% and 80% by volume, respectively, and fluorescence was measured. FIG. 6 is a plot of the change in fluorescence peak intensity as water content increases versus water content in ethanol (v/v%). As shown in FIG. 6, as the percentage of water in ethanol increases from 5% to 80%, the fluorescence peak intensity gradually decreases, and there is a linear relationship between the water content and the fluorescence peak intensity, and the correlation coefficient R 2 =0.9990, detection limit is 0.47%, detection range is 5% -80%; it can be seen that with the addition of water, the fluorescence quenched, the fluorescent reagent was able to detect the water content in ethanol.
Example 6
In acetone solvent, neutral red derivative changes color with increasing water content of the acetone/water mixed solution.
The neutral red derivative prepared in example 1 was dissolved in methylene chloride to prepare a stock solution of 1mg/mL, 100. Mu.L of the stock solution was taken out and added to a 10mL cuvette, and 0mL, 0.2mL, 0.5mL, 1mL, 2.0mL, 3.0mL, 5.0mL, 7.0mL, 8.0mL and 9.0mL of deionized water were added to the 10mL cuvette to prepare a water/acetone solution of 0%,2%,5%,10%,20%,30%,50%,70%,80% and 90% by volume, and the fluorescence change was observed under a 365nm ultraviolet light of natural light. As can be seen from fig. 9, the addition of 2% water to the acetone solvent caused a color change in the solution, which was evident both in natural light and in a 365nm uv lamp, indicating that the water content could be detected colorimetrically in acetone.
While the basic principles, principal features and advantages of the present invention have been described in the foregoing examples, it will be appreciated by those skilled in the art that the present invention is not limited by the foregoing examples, but is merely illustrative of the principles of the invention, and various changes and modifications can be made without departing from the scope of the invention, which is defined by the appended claims.
Claims (3)
1. A fluorescent reagent for detecting the water content in an organic solvent, characterized in that: the fluorescent reagent is a neutral red derivative, and the corresponding chemical structural formula is as follows:
2. a method for preparing a fluorescent reagent for detecting the water content in an organic solvent according to claim 1, which is characterized by comprising the following specific steps: adding a surfactant solution and a neutral red solution into a colorimetric tube, mixing, standing for reaction for two days, wherein a black substance is generated in the colorimetric tube, and the black substance is a neutral red derivative, wherein the surfactant is sodium dodecyl sulfate; the concentration of sodium dodecyl sulfate in the surfactant solution and the concentration of neutral red in the neutral red solution are both 0.1mol/L, and the volume ratio of the surfactant solution to the neutral red solution is 1:1.
3. A method for detecting the water content in an organic solvent by using the fluorescent reagent according to claim 1, which is characterized by comprising the following specific steps: when the detection environment is methanol, the neutral red derivative emits orange fluorescence in pure methanol, the fluorescence is weakened to emit orange fluorescence in the presence of water, and the fluorescent indicator can be used for detecting water in methanol; in a titration test of water, along with the addition of water, the fluorescence intensity is reduced sharply, a linear relation exists between the water content and the fluorescence intensity, and the fluorescence indicator can be used for detecting the water content in methanol; when the detection environment is ethanol, the neutral red derivative emits orange fluorescence in the pure ethanol, the fluorescence peak intensity changes under the condition that trace water exists, the fluorescence intensity is reduced along with the addition of water, and the fluorescence indicator can be used for detecting water in the ethanol; in a titration test of water, with the addition of water, there is a linear relationship between water content and fluorescence intensity, and the fluorescent indicator can be used for detecting the water content in ethanol; when the detection condition is acetone, the color of the aqueous solution changes when a small amount of the aqueous solution is added, and the fluorescent indicator can be used for detecting the water content in the acetone by a colorimetric method.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505020A (en) * | 1967-05-25 | 1970-04-07 | Exxon Research Engineering Co | Method and composition for detecting free water |
| US4380666A (en) * | 1981-07-06 | 1983-04-19 | Eastman Kodak Company | Color-forming sulfonamidodiphenylamine dye precursor that produces phenazine dye |
| US6057120A (en) * | 1996-09-24 | 2000-05-02 | Roche Diagnostics Gmbh | Redox-active compounds and their use |
| CN103242249A (en) * | 2013-05-30 | 2013-08-14 | 杨文龙 | Compound capable of identifying dodecylbenzene sulfonic acid ions as well as preparation method and application thereof |
| WO2022111833A1 (en) * | 2020-11-30 | 2022-06-02 | Cmblu Energy Ag | Electrolyte regeneration for organic redox flow batteries based on water-soluble phenazine-based compounds |
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- 2022-06-11 CN CN202210655515.XA patent/CN115141152B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505020A (en) * | 1967-05-25 | 1970-04-07 | Exxon Research Engineering Co | Method and composition for detecting free water |
| US4380666A (en) * | 1981-07-06 | 1983-04-19 | Eastman Kodak Company | Color-forming sulfonamidodiphenylamine dye precursor that produces phenazine dye |
| US6057120A (en) * | 1996-09-24 | 2000-05-02 | Roche Diagnostics Gmbh | Redox-active compounds and their use |
| CN103242249A (en) * | 2013-05-30 | 2013-08-14 | 杨文龙 | Compound capable of identifying dodecylbenzene sulfonic acid ions as well as preparation method and application thereof |
| WO2022111833A1 (en) * | 2020-11-30 | 2022-06-02 | Cmblu Energy Ag | Electrolyte regeneration for organic redox flow batteries based on water-soluble phenazine-based compounds |
Non-Patent Citations (1)
| Title |
|---|
| 中性红在不同环境和超分子体系中的光谱性质;杨昌英 等;《三峡大学学报(自然科学版)》;第29卷(第01期);第63-65、69页 * |
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