CN110724520A - Fluorescent probe for detecting water content in heavy water and application thereof - Google Patents
Fluorescent probe for detecting water content in heavy water and application thereof Download PDFInfo
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- CN110724520A CN110724520A CN201910898737.2A CN201910898737A CN110724520A CN 110724520 A CN110724520 A CN 110724520A CN 201910898737 A CN201910898737 A CN 201910898737A CN 110724520 A CN110724520 A CN 110724520A
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
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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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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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
- 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 provides a fluorescent probe for detecting the light water content in heavy water, which comprises the following components in percentage by weight:. The fluorescent probe provided by the invention takes the hydroxyl groups of coumarin and xanthene parts as response sites based on the difference of the pH values of heavy water and light water. The fluorescent probe for detecting the light water content in the heavy water can be obtained by chemical synthesis, the synthesis process is simple and feasible, the raw materials are cheap and easy to obtain, the preparation cost is low, and the popularization is easy. The probe has high sensitivity, is basically not interfered by other components in the process of detecting the light water content in corresponding heavy water, and has wide application prospect. The probe has good fluorescence emission spectrum characteristic, and can realize fast light water content in heavy waterThe purpose of quick accurate detection.
Description
Technical Field
The invention belongs to the field of organic small-molecule fluorescent probes, and particularly relates to a fluorescent probe for detecting water content in heavy water based on coumarin and xanthene structures.
Background
Heavy water (Deuterium oxide) is a compound consisting of Deuterium and oxygen, formula D2O, relative molecular mass 20.0275, specific water (H)2O) has a molecular weight 18.0153 about 11% higher, hence the name heavy water. In natural water, the content of heavy water is about 0.015%. Heavy water is also very similar to regular water because deuterium has very little difference in properties from hydrogen.
The special value of heavy water is reflected in the application of atomic energy technology, and heavy water is required to be used as a moderator in nuclear fission reaction for manufacturing powerful nuclear weapons. Where the solvent is water and the subject of investigation is hydrogen, heavy water may be used as the solvent in the nmr analysis. Neutron moderator: some nuclear reactors use heavy water to slow the neutrons down, giving them an opportunity to react with uranium. Light water can also be used as a moderator, but because light water absorbs neutrons, light water reactors must use enriched uranium instead of normal uranium, or the critical mass cannot be reached. Heavy water reactors can use not only ordinary uranium, but also uranium 238 to convert it to plutonium, which can be used to make nuclear bombs. Although heavy water has important use value, it is harmful to human beings, and microorganisms and fish in pure heavy water or water with heavy water (more than 80%) die in hours. In contrast, light water with particularly little heavy water, such as snow water, can stimulate biological growth.
Since heavy water is generally prepared by distillation from light water at present, and heavy water has strong hydrophilicity, a certain amount of light water is often contained in heavy water. The detection of the light water content in the heavy water is of great significance for the safe application of the heavy water. Compared with the traditional detection methods such as atomic absorption and nuclear magnetic resonance, the fluorescence analysis method has the advantages of high sensitivity, good selectivity, quick response, simple operation and the like, and is widely used for detecting various small molecules. Therefore, the development of a new fluorescent probe which has high sensitivity and light stability and can quickly detect the light water content in the heavy water in real time has important significance.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides the fluorescent probe for detecting the water content in the heavy water, which has the advantages of high response speed and strong anti-interference capability.
In order to achieve the purpose, the invention adopts the following technical scheme.
A fluorescent probe for detecting the content of light water in heavy water has a chemical structural formula shown as a formula (I):
formula (I).
The preparation method of the fluorescent probe comprises the following steps:
under the protection of nitrogen, 7-hydroxycoumarin andreacting in DMF (N, N-dimethylformamide) in the presence of HOBT (1-hydroxy-benzo-triazole), EDC (1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride) and DIEA (N, N-diisopropylethylamine), and separating and purifying to obtain the final product.
An application of the fluorescent probe in detecting the light water content in heavy water.
The mechanism of the invention is as follows:
the fluorescent probe provided by the invention takes the hydroxyl groups of coumarin and xanthene parts as response sites based on the difference of the pH values of heavy water and light water. Under the condition of low water content in the heavy water, hydroxyl of the coumarin is ionized into oxyanion, and the xanthene part is converted into a closed-loop structure, so that the fluorescent probe can emit blue fluorescence (the peak value is about 450 nm) of the coumarin part and green fluorescence (the peak value is about 550 nm) of the xanthene part.
The invention has the following advantages:
the fluorescent probe for detecting the light water content in the heavy water can be obtained by chemical synthesis, the synthesis process is simple and feasible, the raw materials are cheap and easy to obtain, the preparation cost is low, and the popularization is easy. The probe has high sensitivity, is basically not interfered by other components in the process of detecting the light water content in corresponding heavy water, and has wide application prospect. The probe has good fluorescence emission spectrum characteristics, and can realize the purpose of quickly and accurately detecting the light water content in the heavy water.
Drawings
FIG. 1 shows a fluorescent probe1H NMR spectrum;
FIG. 2 is a fluorescence spectrum of a fluorescent probe in heavy water of different light water contents;
FIG. 3 is a fluorescence intensity ratio I of the solution450The ratio relation with the light water content;
FIG. 4 is a fluorescence intensity ratio I of the solution550The ratio relation with the light water content;
FIG. 5 shows fluorescence spectra of fluorescent probes after reaction with different substances.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
EXAMPLE 1 Synthesis of fluorescent Probe
Compound 1 (80 mg, 0.2 mmol), 7-hydroxycoumarin (40 mg, 0.2 mmol), HOBT (13.5mg, 0.1 mmol), EDC (78 mg, 0.4 mmol) in 4 mL DMF was stirred at room temperature for 10 min, after which 200. mu.L DIEA was added and stirring continued under nitrogen for 5 h, which was then purified by column chromatography over CH2Cl2: CH3OH = 10:1 (v/v) to obtain an orange fluorescent probe with a yield of 65%,1the H NMR spectrum is shown in FIG. 1.
EXAMPLE 2 fluorescent detection of heavy Water with different light Water content by fluorescent Probe
5 mL of a 10. mu.M heavy aqueous solution of the probe containing 0.33% DMSO and containing 10% to 100% of light water was prepared in advance. Then fluorescence detection (lambda) was performedEx= 400 nm); calculating the fluorescence intensity in each system; by analysing fluorescence at 450 nm and 550 nmStrength versus light water content, the response performance of the probe to light water content was evaluated (see fig. 2, 3 and 4). FIGS. 2, 3 and 4 show that the ratio of fluorescence intensity I of the solution increases with the light water content450And I550Gradually decreases, and simultaneously, the light water content and the fluorescence intensity have a better linear relationship.
Example 3 selectivity of fluorescent probes for different ions
5 mL of a 10. mu.M probe-heavy aqueous solution containing 0.33% DMSO was prepared in advance, and 50. mu.L of 200. mu.M CuSO was sequentially added to the system4、Na2S、Na2SO3、H2O2、Cys、GSH、NaNO2Etc. small molecule aqueous solution. Then fluorescence detection (lambda) was performedEx= 400 nm); the fluorescence intensity I in each system was calculated550And I440(ii) a The different substances were evaluated for their interference with the fluorescent probe solution (see FIG. 5). As can be seen from the figure, of course, CuSO was added to the probe solution4、Na2S and other small molecules, the fluorescence of the solution is basically unchanged.
Claims (3)
3. Use of the fluorescent probe of claim 1 for detecting light water content in heavy water.
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Citations (8)
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CN106243122A (en) * | 2016-08-01 | 2016-12-21 | 济南大学 | A kind of fluorescent probe detecting hydrazine and application thereof |
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CN109970751A (en) * | 2019-04-04 | 2019-07-05 | 济南大学 | A kind of double site, highly sensitive pH fluorescence probe and its synthesis and application |
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Patent Citations (9)
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CN105917234A (en) * | 2014-01-17 | 2016-08-31 | 梅托珍尼克斯株式会社 | Iron(II) ion detection agent and detection method using same |
CN105693703A (en) * | 2016-01-25 | 2016-06-22 | 济南大学 | Novel rate type fluorescent probe for intracellular lysosome pH imaging |
CN105694857A (en) * | 2016-03-18 | 2016-06-22 | 济南大学 | Nitrosyl hydrogen molecular fluorescent probe for mitochondria targeting and preparation method and application thereof |
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CN109970751A (en) * | 2019-04-04 | 2019-07-05 | 济南大学 | A kind of double site, highly sensitive pH fluorescence probe and its synthesis and application |
CN110105376A (en) * | 2019-06-10 | 2019-08-09 | 山西大学 | A kind of fluorescein derivative and its synthetic method and application |
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MINGGANG TIAN 等: "A dual-site controlled ratiometric probe revealing the simultaneous down-regulation of pH in lysosomes and cytoplasm during autophagy", 《CHEM. COMMUN.》 * |
MINGGANG TIAN等: "Unique pH-Sensitive RNA Binder for Ratiometric Visualization of Cell Apoptosis", 《ANAL. CHEM.》 * |
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