CN116444465B - Naphthalene ring fluorescent probe for detecting water content in organic solvent - Google Patents
Naphthalene ring fluorescent probe for detecting water content in organic solvent Download PDFInfo
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- CN116444465B CN116444465B CN202210003411.0A CN202210003411A CN116444465B CN 116444465 B CN116444465 B CN 116444465B CN 202210003411 A CN202210003411 A CN 202210003411A CN 116444465 B CN116444465 B CN 116444465B
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- water content
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- organic solvent
- naphthalene ring
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 31
- 239000003960 organic solvent Substances 0.000 title claims abstract description 18
- 125000001624 naphthyl group Chemical group 0.000 title claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a naphthalene ring fluorescent probe for detecting the water content in an organic solvent, which has the following specific chemical structural formula:
Description
Technical Field
The invention relates to a naphthalene ring fluorescent probe for detecting the water content in an organic solvent and application thereof in determining the water content in the organic solvent.
Background
Water is a common impurity in organic solvents and has important influence on chemical reactions, chemical production and the like. The water content in the organic solvent can have a great influence on the application range of the solvent, for example, the active quenching of the metal organic compound can be caused or a violent reaction can be caused to generate fire or explosion, so that safety accidents are caused. For example, tetrahydrofuran or diethyl ether, which are solvents of the grignard reaction, must be subjected to a strict anhydrous treatment before use, and experimental safety accidents may be caused if the water content exceeds a certain level. Therefore, the rapid determination of the trace water content in the organic solvent is very important for industrial production. The karl fischer method is widely used for quantitative analysis of water content in the liquid phase, but requires specialized equipment and trained operators.
The organic fluorescent probe detection method has the advantages of simple operation, high sensitivity, good selectivity and color response to a detection object, and is attractive for researchers, and the fluorescent probe is developed and has good significance for measuring the water content in an organic solvent.
Disclosure of Invention
The invention aims to provide a naphthalene ring fluorescent probe for detecting the water content in an organic solvent, which is suitable for determining the water content in the organic solvent.
More specifically, the invention relates to a naphthalene ring fluorescent probe for detecting the water content in an organic solvent, which is represented by the following formula:
drawings
FIG. 1 shows the change in fluorescence intensity of the fluorescent probe of the present invention in tetrahydrofuran solvents having different water contents. Embedding diagram: water content in tetrahydrofuran solvent.
FIG. 2 is a standard curve of fluorescence intensity of a fluorescent probe (10. Mu.M) of the present invention with respect to water content in tetrahydrofuran solvent.
FIG. 3 shows the change in fluorescence intensity of the fluorescent probe of the present invention in acetone solvents with different water contents. Embedding diagram: water content in acetonitrile solvent.
FIG. 4 is a standard curve of fluorescence intensity of the fluorescent probe (10. Mu.M) of the present invention with respect to water content in acetone solvent.
FIG. 5 shows the color change of the solution of the fluorescent probe of the present invention in tetrahydrofuran (water contents of 0%,0.2%,0.4%,0.6%,0.8%, 1%) with different water contents under 365nm ultraviolet lamp.
FIG. 6 is a standard curve of R/G values as a function of water content in tetrahydrofuran solvent among RGB values of color photographs of fluorescent probe solutions of the present invention.
FIG. 7 shows the color change of the fluorescent probe of the present invention in acetone with different water contents (water contents of 0%,0.5%,1.0%,1.5%,2.0%,2.5%,3.0% from left to right) under 365nm ultraviolet lamp.
FIG. 8 is a standard curve of R/B values as a function of water content in an acetone solvent among RGB values of color photographs of fluorescent probe solutions of the present invention.
Detailed Description
Example 1 naphthalene ring fluorescent probe for detecting Water content in organic solvent
The synthetic route is shown in the following formula:
compound 1 (1.09 g,5.00 mmol), compound 2 (1.00 g,5.00 mmol), dichloromethane (50 mL) were added to a 100mL three-necked flask, a solution of NaOH (0.20 g,5.00 mmol) in ethanol (10 mL) was added dropwise, the mixture was heated to 40℃and reacted for 4 hours, hydrochloric acid was slowly added dropwise to the reaction mixture to neutralize, water was added, the organic phase was dried over anhydrous magnesium sulfate, and the filtrate was filtered to remove the solvent to give Compound 3 as a yellow solid. Compound 3 (0.80 g,2.00 mmol), D-glucose (0.72 g,4.00 mmol), KOH (0.45 g,8.00 mmol), water (5 mL), DMSO (10 mL) were added to a 50mL three-necked flask, heated to 110℃and reacted for 6 hours, a large amount of water was added to the reaction solution, extracted three times (3X 50 mL) with ethyl acetate, washed three times (3X 40 mL) with saturated saline, and dried over anhydrous magnesium sulfate. Silica gel column chromatography (petroleum ether: ethyl acetate=3:1) gives an orange solid, which gives the target compound 4 in 41% yield.
The product is characterized by nuclear magnetic hydrogen spectrum, nuclear magnetic carbon spectrum and high-resolution mass spectrum.
1 H NMR(300MHz，DMSO)δ8.78(s，1H)，8.16-8.06(m，2H)，7.94(d，J＝8.6Hz，1H)，7.81-7.53(m，4H)，7.43(s，1H)，7.28(d，J＝8.8Hz，1H)，7.15(d，J＝2.9Hz，1H)，6.85(d，J＝2.9Hz，1H)，6.66(d，J＝8.2Hz，2H)，5.62(s，2H)，3.93(s，3H).
13 C NMR(75MHz，DMSO)δ188.1，159.8，158.3，150.4，149.8，137.3，133.7，131.8，130.3，130.2，128.1，127.3，126.5，125.3，121.3，119.9，117.4，116.7，114.3，106.6，106.0，55.6.
High resolution: c (C) 24 H 20 NO 3 [M+H] + : theoretical values: 370.143770; actual values: 370.143691.
example 2 determination of the Water content in organic solvents by naphthalene Ring fluorescent probes of the invention
The change of the fluorescence intensity of the fluorescent probe in tetrahydrofuran solvents with different water contents is shown in figure 1, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) and the water content in the tetrahydrofuran solvents can be made according to the change, the linear range is 0% -1% of the water content, the standard curve is shown in figure 2, and the fluorescent probe can be used for quantitative detection of the water content in the tetrahydrofuran solvents through establishment of the standard curve.
The change of the fluorescence intensity of the fluorescent probe in the acetone solvent with different water contents is shown in figure 3, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) and the water content in the acetone solvent can be made according to the change, the linear range is 0% -1% of the water content, the standard curve is shown in figure 4, and the fluorescent probe can be used for quantitatively detecting the water content in the acetone solvent through the establishment of the standard curve.
The color change of the solution of the fluorescent probe in tetrahydrofuran with different water contents (the water contents are 0%,0.2%,0.4%,0.6%,0.8% and 1% from left to right) is shown in figure 5. The color of the fluorescent probe solution of the present invention gradually changes from bright yellow to earthy yellow as the water content of tetrahydrofuran increases. The RGB values of the probe in different solvent photos are read through the mobile phone color extractor APP, and the R/G value of the solvent photo and the water content in the tetrahydrofuran solvent are found to have good linear relation (figure 6), so that the method can be used for detecting the water content in the tetrahydrofuran solvent.
The color change of the solution of the fluorescent probe in acetone with different water contents (the water contents are 0%,0.5%,1.0%,1.5%,2.0%,2.5% and 3.0% from left to right) is shown in fig. 7. The color of the fluorescent probe solution of the present invention gradually changes from bright yellow to dark yellow as the water content of the acetone increases. The RGB values of the probe in different solvent photos are read through the mobile phone color extractor APP, and the R/B value of the solvent photo and the water content in the acetone solvent are found to have good linear relation (figure 8), so that the method can be used for detecting the water content in the acetone solvent.
According to the embodiment 2, the naphthalene nucleus fluorescent probe for detecting the water content in the organic solvent can be proved to realize the rapid determination of the water content in the organic solvent by a common smart phone under the condition of not needing any special instrument and equipment.
Claims (1)
1. A naphthalene ring fluorescent probe for detecting the water content in an organic solvent has a specific chemical structural formula as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202210003411.0A CN116444465B (en) | 2022-01-05 | 2022-01-05 | Naphthalene ring fluorescent probe for detecting water content in organic solvent |
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| CN202210003411.0A CN116444465B (en) | 2022-01-05 | 2022-01-05 | Naphthalene ring fluorescent probe for detecting water content in organic solvent |
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| CN116444465B true CN116444465B (en) | 2024-01-26 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111607390A (en) * | 2020-06-02 | 2020-09-01 | 中国林业科学研究院林产化学工业研究所 | Application of dehydroabietic acid triarylamine D-pi-A compound as fluorescent probe to detection of water content in solvent |
| CN113248512A (en) * | 2021-06-17 | 2021-08-13 | 广州汇标检测技术中心 | Fluorescent probe for detecting trace water in organic solvent and preparation method and application thereof |
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- 2022-01-05 CN CN202210003411.0A patent/CN116444465B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111607390A (en) * | 2020-06-02 | 2020-09-01 | 中国林业科学研究院林产化学工业研究所 | Application of dehydroabietic acid triarylamine D-pi-A compound as fluorescent probe to detection of water content in solvent |
| CN113248512A (en) * | 2021-06-17 | 2021-08-13 | 广州汇标检测技术中心 | Fluorescent probe for detecting trace water in organic solvent and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| A novel fluorescence probe for the detection of water content in organic solvents and the distinction between deuterated and nondeuterated reagents;Bing Deng 等;Lumines cence;全文 * |
| 一种新型极性荧光探针的合成与应用;张妍;牛承岗;曾光明;秦品珠;李慧霞;彭博;;分析试验室(09);全文 * |
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