CN114989081A - Colorimetric probe and preparation method and application thereof - Google Patents
Colorimetric probe and preparation method and application thereof Download PDFInfo
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- CN114989081A CN114989081A CN202210503722.3A CN202210503722A CN114989081A CN 114989081 A CN114989081 A CN 114989081A CN 202210503722 A CN202210503722 A CN 202210503722A CN 114989081 A CN114989081 A CN 114989081A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
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- 238000010521 absorption reaction Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 15
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 35
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- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 229940126214 compound 3 Drugs 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 229940125904 compound 1 Drugs 0.000 claims description 20
- 229940125782 compound 2 Drugs 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 19
- 238000004440 column chromatography Methods 0.000 claims description 18
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000005457 ice water Substances 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
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- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 230000001335 demethylating effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002081 enamines Chemical class 0.000 claims description 5
- 238000006170 formylation reaction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000004451 qualitative analysis Methods 0.000 claims description 3
- 238000004445 quantitative analysis Methods 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
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- 239000007858 starting material Substances 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 229910000397 disodium phosphate Inorganic materials 0.000 claims 1
- 235000019800 disodium phosphate Nutrition 0.000 claims 1
- 239000001488 sodium phosphate Substances 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 27
- 230000008859 change Effects 0.000 abstract description 23
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- -1 triphenylamine modified quinoline salt compound Chemical class 0.000 abstract description 2
- 229920002554 vinyl polymer Polymers 0.000 abstract description 2
- 230000000007 visual effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 79
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000012360 testing method Methods 0.000 description 12
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- 238000005481 NMR spectroscopy Methods 0.000 description 5
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- MVIPGWFTBPVNBJ-UHFFFAOYSA-N 3-methoxy-n,n-diphenylaniline Chemical compound COC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MVIPGWFTBPVNBJ-UHFFFAOYSA-N 0.000 description 4
- XLZCIXFPTHCUFB-UHFFFAOYSA-N dmf pocl3 Chemical compound CN(C)C=O.ClP(Cl)(Cl)=O XLZCIXFPTHCUFB-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- 125000002524 organometallic group Chemical group 0.000 description 2
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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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- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- General Health & Medical Sciences (AREA)
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Abstract
The invention provides a colorimetric probe and a preparation method and application thereof. The colorimetric probe is 2- [2- (4-diphenylamine-2-hydroxy-phenyl) -vinyl ] -1-ethyl-quinoline salt iodide, a triphenylamine modified quinoline salt compound is used as a fluorophore, intramolecular hydroxyl is used as a detection site, the maximum ultraviolet absorption wavelength of the colorimetric probe is subjected to red shift along with the increase of water content in a solvent in the presence of disodium hydrogen phosphate, the ratio of the maximum ultraviolet absorption wavelength to the maximum ultraviolet absorption wavelength is increased along with the increase of the water content, the color change of the solution is large, and the detection of trace water in the solvent is realized by monitoring the change of an ultraviolet visible absorption spectrum. Compared with the prior art, the colorimetric probe has the characteristics of high sensitivity, good selectivity, high response speed and the like, can be used for detecting trace water, can be used for quickly identifying and visualizing the color change of the trace water with naked eyes, can realize visual detection, and has good potential application prospect. And the colorimetric probe of the invention has simple preparation method, easy operation and convenient popularization and application.
Description
Technical Field
The invention relates to the technical field of chemical analysis and detection, in particular to a colorimetric probe and a preparation method and application thereof.
Background
In many organic solvents, water is generally considered an impurity, and therefore its measurement in solvents is of great importance for many industrial processes, food processing, biomedicine and environmental monitoring. For example, in chemistry, particularly in organometallic chemistry, the presence of water can cause the reactive metal organic compound to quench, inhibit the reaction, or reduce the yield. Furthermore, due to the high reactivity of some organometallic reagents, the presence of water can, in some cases, lead to catastrophic events such as fires and explosions. In certain industrial processes, water plays a detrimental role, one example of which is petroleum-based fuels. The presence of water can lead to reduced engine performance, but more importantly, when the temperature is low enough, emulsification and phase separation can occur, clogging the fuel lines, leading to engine damage and failure. Manufacturers of solvents and chemicals must ensure that their products have low moisture levels to meet customer needs, etc.
Until now, various methods have been used to determine water content, including karl fischer (anal. chem.,1990,62,2504), flood analysis (FIA) (anal. chem.,1996,68,971), electrochemical and electrophysical sensing mechanisms (sens. actual a-physics, 2005,118,202), and the like. However, most of the detection methods require complicated processing, complicated operation, expensive large-scale instruments and equipment, long time consumption and the like. Is not beneficial to real-time field monitoring. In addition, several publications have reported colorimetric, fluorescent probes for water content detection in solvents, such as chem.commun.,2020,56, 1191-; ACS Sustain. chem. Eng.,2020,8,23, 8857-8867; ACS Omega, 2019,4, 10695-; chem.Soc.Rev.,2016,45, 1242-1256; RSC adv.,2015, 5,12191; RSC adv.,2014,4,21608; RSC adv.,2014,4, 25330; RSC adv., 2013,3, 23255-23263; chem. commun.,2012,48, 3933-; dye pigment, 2012,92, 1199-; dye pigment, 2011,88, 307; org.biomol.chem.,2011, 9, 1314; Photochem.Photobiol.A-chem.2011, 222, 52-55; sens. actual B-chem.,2011,157,14-18, and the like. However, these colorimetric and fluorescent probes have the disadvantages of long response time, low sensitivity, high detection limit, insignificant color change, etc., which severely limits the practical application of these probes. Therefore, the development of colorimetric probes with simple operation, high detection sensitivity and obvious color change for detecting trace water in the organic solvent has important significance.
Disclosure of Invention
The invention aims to provide a colorimetric probe and a preparation method and application thereof aiming at the defects in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect of the present invention, a colorimetric probe is provided, wherein the colorimetric probe has a structural formula shown in formula I:
the second object of the present invention is to provide a method for preparing the colorimetric probe, which comprises using the compound 13-methoxytriphenylamine
Is used as a starting material and comprises the following steps:
step S1 demethylating compound 1 to give compound 2, having the formula:
in step S2, compound 1 undergoes Vilsmeie formylation reaction to produce compound 3, having the structural formula:
step S3, carrying out alkylation reaction on 2-methylquinoline to obtain a compound 4, wherein the structural formula is as follows:
and step S4, mixing the compound 3 and the compound 4, and carrying out enamine reaction to generate the colorimetric probe, wherein the structural formula is shown as a formula I.
Further, the preparation method specifically comprises the following steps:
step S1, dissolving compound 1 in organic solvent, and generating compound 2 in the presence of demethylating reagent;
step S2, performing Vilsmeie formylation reaction on the compound 2 obtained in the step S1 in a solvent in the presence of an acylating agent and a catalyst, and treating after the reaction to obtain a compound 3;
step S3, dissolving 2-methylquinoline and iodoethane in acetonitrile, heating the reaction solution to 85 ℃, stirring for reaction, cooling the reaction solution, precipitating with diethyl ether, and filtering to obtain a compound 4;
and step S4, dissolving the compound 3 obtained in the step S2 and the compound 4 obtained in the step S3 in ethanol, adding a catalyst, heating and refluxing to perform enamine reaction, and processing after the enamine reaction to obtain the colorimetric probe.
Further, the preparation method specifically comprises the following steps:
step S1, dissolving the compound 1 in dichloromethane, dropwise adding a demethylating reagent boron tribromide under the condition of ice bath stirring, reacting overnight at room temperature, dropwise adding the reaction solution into ice water after the reaction is finished, adjusting the pH value with a saturated sodium bicarbonate solution, washing with water, drying and concentrating an organic phase through anhydrous sodium sulfate, and purifying a concentrated crude product through column chromatography to obtain a compound 2;
step S2, dissolving the compound 2 obtained in the step S1 in N, N-dimethylformamide, dropwise adding an N, N-dimethylformamide solution of phosphorus oxychloride under the condition of ice bath stirring, reacting for 2-3 hours, adding water, hydrolyzing for 2-3 hours, washing with water, drying and concentrating an organic phase through anhydrous sodium sulfate, and purifying a concentrated crude product through column chromatography to obtain a compound 3;
step S3, dissolving 2-methylquinoline and iodoethane in acetonitrile, heating for reaction for a period of time, cooling with ice water, precipitating with diethyl ether, and filtering to obtain a compound 4;
and step S4, dissolving the compound 3 obtained in the step S2 and the compound 4 obtained in the step S3 in ethanol, adding a catalyst of pyrrolidine, heating and refluxing for reaction for a period of time, cooling to room temperature, concentrating, purifying a reaction crude product by column chromatography, and drying in vacuum to obtain the compound colorimetric probe.
Further, in step S1, the molar ratio of compound 1 to boron tribromide is 1mmol (15-25) mmol, the molar volume ratio of compound 1 to dichloromethane is 1mmol: (10-15) mL, the molar volume ratio of the compound 1 to the sodium bicarbonate solution is 1mmol: (4-6) mL.
Further, in step S2, the molar ratio of compound 2 to phosphorus oxychloride is 1mmol (2-4) mmol, the molar volume ratio of compound 1 to N, N-dimethylformamide is 1mmol: (2-4) mL.
Further, in step S3, the molar ratio of 2-methylquinoline to iodoethane is 1mmol (1.5-2.5) mmol, the molar volume ratio of 2-methylquinoline to acetonitrile is 1mmol: (5-10) mL, heating the reaction temperature to 80-85 ℃, and reacting for 18-24 hours.
Further, in step S4, the molar ratio of compound 3 to compound 4 is 1mmol: (1.2-2) mmol, the molar volume ratio of the compound 3 to the tetrahydropyrrole is 1mmol: (0.1-0.3) mL, the molar volume ratio of the compound 4 to the ethanol is 1mmol: (10-15) mL, heating the reaction temperature to 80-85 ℃, and reacting for 8-12 hours.
The third purpose of the invention is to provide the application of the colorimetric probe, which is used for qualitative and quantitative analysis of trace water in a solvent.
Further, the colorimetric probe reacts with water molecules in the solution in the presence of disodium hydrogen phosphate, so that the maximum ultraviolet absorption wavelength of the colorimetric probe is subjected to red shift.
Compared with the prior art, the invention has the following beneficial effects:
(1) the colorimetric probe provided by the invention is 2- [2- (4-diphenylamine-2-hydroxy-phenyl) -vinyl ] -1-ethyl-quinoline salt iodide, a triphenylamine modified quinoline salt compound is used as a fluorescent group, intramolecular hydroxyl is used as a detection site, the maximum ultraviolet absorption wavelength of the colorimetric probe is subjected to red shift along with the increase of water content in a solvent in the presence of disodium hydrogen phosphate, the ratio is increased along with the increase of the water content, the color change of the solution is large, the detection of trace water in the solvent is realized by monitoring the ultraviolet visible absorption spectrum change, the colorimetric probe can be used as a novel detection reagent for detecting the trace water, the colorimetric and quantitative detection can be performed on the trace water in a sample, and the colorimetric probe has wide application prospect,
(2) the colorimetric probe prepared by the invention has the advantages of simple preparation method, easy operation and convenient popularization and application;
(3) the colorimetric probe can be used for detecting trace water, can be quickly identified, can be used for detecting the color change of the trace water by naked eyes, and can realize visual detection;
(4) the colorimetric probe prepared by the method can generate quick response to trace water in a solution, realizes spectrum and colorimetric dual-mode detection, does not need sample pretreatment, and is very simple to detect;
(5) the colorimetric probe provided by the invention can provide a wider detection range, is suitable for various solvents such as DMSO, methanol, ethanol and the like, and has high sensitivity which can reach 100ppm at most.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a colorimetric probe in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of the colorimetric probe of example 1 of the present invention;
FIG. 3 is a mass spectrum of a colorimetric probe in example 1 of the present invention;
FIG. 4a is a UV-VIS test chart of the colorimetric probe prepared in example 1 for detecting trace amounts of water in DMSO solution;
FIG. 4b is a linear relationship graph of colorimetric probe absorbance ratio versus water content in DMSO solution;
FIG. 5a is a UV-VIS absorption spectrum test chart of the colorimetric probe prepared in example 1 for detecting trace amounts of water in a methanol solution;
FIG. 5b is a graph of the linear relationship between the colorimetric probe absorbance ratio and water content in methanol solution;
FIG. 6a is a UV-VIS absorption spectrum test chart of the colorimetric probe prepared in example 1 for detecting trace water in ethanol solution;
FIG. 6b is a graph of the linear relationship between the colorimetric probe absorbance ratio and water content in ethanol solution;
FIG. 7 is a photograph showing a color change of the colorimetric probe prepared in example 1 in a DMSO solution;
FIG. 8 is a photograph showing a color change of the colorimetric probe prepared in example 1 in a methanol solution;
FIG. 9 is a photograph showing a color change of the colorimetric probe prepared in example 1 in an ethanol solution.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention are described in further detail below with reference to specific examples and accompanying drawings.
The colorimetric probe provided by the invention has a structural formula shown as a formula I, and a molecular formula C 31 H 27 IN 2 O, with a relative molecular mass of 570.46, is a black purple solid powder, and is dissolved in solvents such as DMSO, DMF, chloroform, etc.
The synthetic route of the colorimetric probe of the present invention is as follows:
example 1
The preparation method of the colorimetric probe comprises the following steps:
step S1, dissolving 1.9g of compound 1 (3-methoxytriphenylamine) in 10mL of dichloromethane, dropwise adding 10.1mL of boron tribromide by using an injector under the condition of ice bath and stirring, reacting at room temperature overnight, dropwise adding the reaction solution into 100mL of ice water after the reaction is finished, adjusting the pH to be neutral by using 24mL of saturated sodium bicarbonate solution, washing for three times by using water, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a reaction crude product by using column chromatography to obtain 1.65g of compound 2, wherein the yield is 91.6%;
step S2, dissolving 783mg of compound 2 in 6mL of N, N-dimethylformamide, dripping 6mmol of phosphorus oxychloride N, N-dimethylformamide (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) into the reaction solution by using an injection under the condition of ice bath stirring, reacting for 2 hours, adding water for hydrolysis for 2.5 hours, washing with water for three times, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a crude reaction product by using column chromatography to obtain 687mg of light green compound 3, wherein the yield is 79.2%.
Step S3, dissolving 1.43g of 2-methylquinoline and 2.34g of iodoethane in acetonitrile, heating to 80 ℃ for reacting for 18h, cooling by ice water, precipitating by diethyl ether, and filtering to obtain 2.56g of black red compound 4, wherein the yield is 85.6%;
step S4, compound 3 289mg and compound 4 358.8mg are dissolved in 10mL of ethanol, 100 μ L of tetrahydropyrrole is added, the mixture is heated and refluxed at 80 ℃ for 8 hours, the mixture is cooled to room temperature and then concentrated, and the reaction crude product is purified by column chromatography to obtain 476mg of deep purple compound as a colorimetric probe, with the yield of 83.5%.
A structure confirmation study was performed on the colorimetric probe obtained in example 1:
as shown in fig. 1, the nmr spectrum of the colorimetric probe is characterized by: 1 H NMR(500 MHz,DMSO)δ10.61(s,1H),8.77(d,J＝9.1Hz,1H),8.41(dd,J＝19.4,9.1 Hz,1H),8.27–8.19(m,1H),8.05(t,J＝7.6Hz,1H),7.80(t,J＝7.5Hz,1H), 7.70(d,J＝8.8Hz,1H),7.63(d,J＝15.5Hz,1H),7.37(t,J＝7.8Hz,1H),7.22 –7.10(m,2H),6.39(d,J＝2.1Hz,1H),6.33(dd,J＝8.8,2.0Hz,1H),4.90(dd, J＝13.8,6.7Hz,1H),1.48(t,J＝7.2Hz,1H)。
as shown in fig. 2, the nuclear magnetic resonance carbon spectrum of the colorimetric probe is characterized by the following structural features: 13 C NMR(500 MHz,DMSO)δ160.02,156.17,152.85,146.08,144.48,143.22,138.57,135.10, 132.46,130.69,130.40,128.71,127.83,126.89,125.80,120.90,118.95,115.58, 113.89,111.80,105.87,46.51,14.04。
as shown in FIG. 3, molecular weight-assisted proof by high resolution mass spectrometry was performed, HRMS (ESI): M/z 444.2803[ M + H] + 。
Colorimetric Probe of the present invention, C 31 H 27 IN 2 O, the Chinese name: 2- [2- (4-Diphenylamine-2-hydroxy-phenyl) -ethenyl]-1-ethyl-quinolinate iodide, molecular weight 570.46.
Successful synthesis of the colorimetric probe can be confirmed by nuclear magnetic and mass spectrometry analysis.
Example 2
The preparation method of the colorimetric probe comprises the following steps:
step S1, dissolving 1.9g of compound 1 (3-methoxytriphenylamine) in 12mL of dichloromethane, dropwise adding 14.0mL of boron tribromide by using an injector under the condition of ice bath and stirring, reacting at room temperature overnight, dropwise adding the reaction solution into 120mL of ice water after the reaction is finished, adjusting the pH to be neutral by using 28mL of saturated sodium bicarbonate solution, washing for three times by using water, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a reaction crude product by using column chromatography to obtain 1.75g of compound 2, wherein the yield is 97.2%;
step S2, dissolving 783mg of compound 2 in 8mL of N, N-dimethylformamide, dripping 8mmol of phosphorus oxychloride N, N-dimethylformamide solution (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) into the reaction solution by using an injection under the condition of ice bath stirring, reacting for 3 hours, adding water for hydrolysis for 2.5 hours, washing with water for three times, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a crude reaction product by column chromatography to obtain 703mg of light green compound 3, wherein the yield is 81.1%.
Step S3, dissolving 1.43g of 2-methylquinoline and 2.81g of iodoethane in acetonitrile, heating to 82 ℃ for reaction for 20h, cooling by ice water, precipitating by diethyl ether, and filtering to obtain 2.47g of black-red compound 4, wherein the yield is 82.6%;
step S4, dissolving 289mg of compound 3 and 418.6mg of compound 4 in 12mL of ethanol, adding 180 μ L of tetrahydropyrrole, heating and refluxing at 82 ℃ for 9 hours, cooling to room temperature, concentrating, and purifying the reaction crude product by column chromatography to obtain 458mg of dark purple compound as a colorimetric probe with a yield of 80.4%.
The detection method provided in example 1 is used to structurally characterize the colorimetric probe provided in example 2, and the characterization result is the same as that in example 1, which can confirm that the colorimetric probe was successfully synthesized.
Example 3
The preparation method of the colorimetric probe comprises the following steps:
step S1, dissolving 1.9g of compound 1 (3-methoxytriphenylamine) in 13mL of dichloromethane, dropwise adding 16.5mL of boron tribromide by using an injector under the condition of ice bath and stirring, reacting at room temperature overnight, dropwise adding the reaction solution into 115mL of ice water after the reaction is finished, adjusting the pH to be neutral by using 29mL of saturated sodium bicarbonate solution, washing for three times by using water, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a reaction crude product by using column chromatography to obtain 1.63g of compound 2, wherein the yield is 90.5%;
step S2, 783mg of compound 2 is dissolved in 10mL of N, N-dimethylformamide, 10mmol of phosphorus oxychloride N, N-dimethylformamide solution (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is dripped into the reaction solution by using an injection under the condition of ice bath stirring, after 3.5 hours of reaction, water is added for hydrolysis for 2.5 hours, after three times of washing, an organic phase is dried and concentrated by using anhydrous sodium sulfate, and a crude reaction product is purified by column chromatography to obtain 722mg of light green compound 3, wherein the yield is 83.3%.
Step S3, dissolving 1.43g of 2-methylquinoline and 3.41g of iodoethane in acetonitrile, heating to 83 ℃ for reaction for 21 hours, cooling by ice water, precipitating by ethyl ether, and filtering to obtain 2.68g of black red compound 4, wherein the yield is 89.6%;
step S4, 289mg of compound 3 and 308.3mg of compound 4 are dissolved in 14mL of ethanol, 240 μ L of tetrahydropyrrole is added, heating reflux is carried out at 83 ℃ for 10 hours, the mixture is cooled to room temperature and then concentrated, and the crude reaction product is purified by column chromatography to obtain 484mg of dark purple compound which is a colorimetric probe, and the yield is 84.9%.
The detection method provided in example 1 is used to structurally characterize the colorimetric probe provided in example 3, the characterization result is the same as that in example 1, and it can be determined that the colorimetric probe was successfully synthesized.
Example 4
The preparation method of the colorimetric probe comprises the following steps:
step S1, dissolving 1.9g of compound 1 (3-methoxytriphenylamine) in 15mL of dichloromethane, dropwise adding 19.5mL of boron tribromide by using an injector under the condition of ice bath and stirring, reacting at room temperature overnight, dropwise adding the reaction solution into 140mL of ice water after the reaction is finished, adjusting the pH to be neutral by using 32mL of saturated sodium bicarbonate solution, washing for three times by using water, drying and concentrating an organic phase by using anhydrous sodium sulfate, and purifying a reaction crude product by using column chromatography to obtain 1.64g of compound 2, wherein the yield is 91.1%;
step S2, 783mg of compound 2 is dissolved in 12mL of N, N-dimethylformamide, 12mmol of phosphorus oxychloride N, N-dimethylformamide solution (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is dripped into the reaction solution by using an injection under the condition of ice bath stirring, after 4.0h of reaction, water is added for hydrolysis for 3.5h, after three times of water washing, an organic phase is dried and concentrated by using anhydrous sodium sulfate, and a crude reaction product is purified by column chromatography to obtain 702mg of light green compound 3, wherein the yield is 80.0%.
Step S3, dissolving 1.43g of 2-methylquinoline and 3.87g of iodoethane in acetonitrile, heating to 85 ℃ for reaction for 24 hours, cooling by ice water, precipitating by diethyl ether, and filtering to obtain 2.67g of black-red compound 4, wherein the yield is 89.2%;
step S4, compound 3 289mg and compound 4 598.8mg are dissolved in 15mL of ethanol, 300 μ L of tetrahydropyrrole is added, heating reflux is performed at 85 ℃ for 12 hours, the mixture is cooled to room temperature and then concentrated, and the reaction crude product is purified by column chromatography to obtain 488mg of deep purple compound, which is a colorimetric probe, and the yield is 85.6%.
The detection method provided in example 1 is used to structurally characterize the colorimetric probe provided in example 4, and the characterization result is the same as that in example 1, which can confirm that the colorimetric probe was successfully synthesized.
To demonstrate that the colorimetric probe of the present invention can be applied to qualitative and quantitative analysis of trace amounts of water in a solvent, the applicant conducted the following studies using the colorimetric probe prepared in example 1:
(1) UV-VIS absorption Spectroscopy testing of colorimetric probes in DMSO systems
Transferring different volumes of ultra-dry dimethyl sulfoxide solution into a cuvette containing auxiliary substance disodium hydrogen phosphate, adding 20 μ L of probe (1mM) mother solution into the solution, shaking the cuvette, placing the cuvette uniformly, transferring different amounts of water into the cuvette with a total volume of 2mL so that the water content (v/v) in the cuvette is 0%, 0.01%, 0.02%, 0.04%, 0.06%, 0.08%, 0.1%, 0.12%, 0.14%, 0.16%, 0.18%, 0.2%, 0.3%, 0.4%, 0.6%, 0.8%, 1%, respectively, and finally shaking the cuvette for 1 minute, and recording the ultraviolet-visible absorption spectrum change of the solution.
As shown in FIG. 4a, the test results show that the absorption peak of the probe compound at 525nm gradually decreases and a new absorption peak at 620nm appears as the water content in the DMSO solution increases. The colorimetric probe can realize the detection of trace water in the dimethyl sulfoxide by monitoring the change of the ultraviolet visible absorption spectrum.
As shown in FIG. 4b, the results show that the ratio I of the water content in the dimethyl sulfoxide solution to the absorption intensity of the probe detection system is in the range of 0-0.16% 620nm /I 525nm In good linear relation, y is 21.44x +0.09, R 2 ＝0.993。
(2) UV-VIS absorption Spectroscopy testing of colorimetric probes in methanol systems
Transferring ultra-dry methanol solutions with different volumes into cuvettes containing auxiliary substance disodium hydrogen phosphate, adding 20 μ L of probe (1mM) mother solution into the solution, shaking the cuvettes and placing them, transferring water with different contents into the cuvettes with a total volume of 2mL so that the water content (v/v) in the cuvettes is 0%, 0.3%, 0.5%, 0.8%, 1.0%, 1.3%, 1.5%, 1.8%, 2.0%, 2.3%, 2.5%, 3.0%, 3.5%, 4.0%, 5.0%, 6.0%, 8.0%, 10%, respectively, shaking the cuvettes and placing them for 1 minute, and recording the change of UV-visible absorption spectrum of the solution.
As shown in FIG. 5a, the test results showed that the probe compound had a gradually decreasing absorption peak at 530nm and a new absorption peak at 585nm with increasing water content in the methanol solution. The colorimetric probe of the present invention can realize the detection of trace water in methanol by monitoring the change of the ultraviolet visible absorption spectrum.
As shown in FIG. 5b, the results show that the ratio I of the water content in the methanol solution to the absorption intensity of the probe detection system is in the range of 0-2.0% 585nm /I 530nm In good linear relationship, y is 0.76x +0.55, R 2 ＝0.993。
(3) Ultraviolet-visible absorption spectrum test of colorimetric probe in ethanol system
Transferring different volumes of ultra-dry ethanol solution into a cuvette containing auxiliary substance disodium hydrogen phosphate, adding 20 microliter of probe (1mM) mother solution into the solution, shaking the cuvette, placing the cuvette uniformly, transferring different contents of water into the cuvette, wherein the total volume is 2mL, so that the contents (v/v) of the water in the cuvette are respectively 0%, 0.01%, 0.02%, 0.04%, 0.06%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.4%, 0.6%, 0.8% and 1%, finally shaking the cuvette, placing the cuvette uniformly for 1 minute, and recording the change of the ultraviolet-visible absorption spectrum of the solution before and after reaction.
As shown in FIG. 6a, the test results show that the probe compound has a gradually decreasing absorption peak at 545nm and a new absorption peak at 595nm as the water content in the ethanol solution increases. The colorimetric probe can realize the detection of trace water in ethanol by monitoring the change of the ultraviolet visible absorption spectrum.
As shown in FIG. 6b, the results indicate that the water content in the ethanol solution is in the range of 0-2.0%, and the ratio I of the water content to the absorption intensity of the probe detection system 595nm /I 545nm In good linear relationship, y is 5.21 x +0.94, R 2 ＝0.992。
(4) Detection of trace water in dimethyl sulfoxide solution
Dissolving colorimetric probe in dimethyl sulfoxide solution to obtain a solution with a concentration of 1 × 10 -3 Transferring different volumes of ultra-dry dimethyl sulfoxide solution into cuvettes containing disodium hydrogen phosphate according to mol/L solution, adding 60 mu L of probe mother solution into the solution, shaking the cuvettes uniformly, transferring different contents of water into the cuvettes with the total volume of 2mL so that the contents (v/v) of water in the cuvettes are respectively 0%, 0.01%, 0.02%, 0.04%, 0.06%, 0.08%, 0.1%, 0.12%, 0.14%, 0.16%, 0.18%, 0.2%, 0.3%, 0.4%, 0.6%, 0.8% and 1%, and finally shaking the cuvettes uniformly and standing for 1 minute to record the color change of the solution system.
As shown in FIG. 7, the test results show that as the water content in the DMSO solution increases, the color of the solution changes from rosy to blue under natural light conditions, indicating that the colorimetric probe of the present invention reacts with water molecules in the DMSO solution in the presence of the auxiliary disodium hydrogen phosphate and causes a color change in the solution.
(5) Detection of trace amounts of water in methanol solutions
Dissolving colorimetric probe in methanol to obtain a solution with a concentration of 1 × 10 -3 Transferring different volumes of ultra-dry methanol solutions into cuvettes containing disodium hydrogen phosphate according to mol/L solution, adding 60 mu L of probe mother liquor into the solution, shaking the cuvettes uniformly, transferring different contents of water into the cuvettes with the total volume of 2mL so that the contents of water (v/v) in the cuvettes are respectively 0%, 0.3%, 0.5%, 0.8%, 1.0%, 1.3%, 1.5%, 1.8%, 2.0%, 2.3%, 2.5%, 3.0%, 3.5%, 4.0%, 5.0%, 6.0%, 8.0%, 10%, shaking the cuvettes uniformly, standing for 1 minute, and recording the color change of the solution system.
As shown in FIG. 8, the test results show that as the water content of the methanol solution increases, the color of the solution changes from purple to blue under natural light conditions, indicating that the colorimetric probe of the present invention reacts with water molecules in the presence of the auxiliary substance disodium hydrogen phosphate in the methanol solution and causes a change in the color of the solution.
(6) Detection of trace water in ethanol solution
Dissolving colorimetric probe in ethanol to obtain a solution with a concentration of 1 × 10 -3 Transferring different volumes of ultra-dry ethanol solutions into cuvettes with disodium hydrogen phosphate, adding 60 mu L of probe mother liquor into the solution, shaking the cuvettes uniformly, transferring different contents of water into the cuvettes with the total volume of 2mL so that the contents (v/v) of water in the cuvettes are respectively 0%, 0.01%, 0.02%, 0.04%, 0.06%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.4%, 0.6%, 0.8% and 1%, finally shaking the cuvettes uniformly, standing for 1 minute, and recording the color change of the solution system.
As shown in FIG. 9, the test results show that as the water content of the ethanol solution increases, the color of the solution changes from bluish purple to blue under natural light conditions, indicating that the colorimetric probe of the present invention reacts with water molecules in the presence of the auxiliary substance disodium hydrogen phosphate in the ethanol solution and causes a change in the color of the solution.
The embodiments and features of the embodiments described herein above may be combined with each other without conflict.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, but rather as the subject matter of the invention is to be construed in all aspects and as broadly as possible, and all changes, equivalents and modifications that fall within the true spirit and scope of the invention are therefore intended to be embraced therein.
Claims (10)
1. A colorimetric probe having a structural formula represented by formula I:
2. a method of preparing a colorimetric probe as defined in claim 1, characterized in that the compound 13-methoxytriphenylamine is used as the preparation method
Is taken as a starting material and comprises the following steps:
s1, demethylating the compound 1 to obtain a compound 2, wherein the structural formula is as follows:
s2, carrying out Vilsmeie formylation reaction on the compound 1 to generate a compound 3, wherein the structural formula is as follows:
s3 and 2-methylquinoline are subjected to alkylation reaction to obtain a compound 4, wherein the structural formula is as follows:
and (3) mixing the S4, the compound 3 and the compound 4, and carrying out enamine reaction to generate a colorimetric probe, wherein the structural formula is shown as a formula I.
3. The method of making a colorimetric probe as claimed in claim 2, wherein the method of making comprises the steps of:
s1, dissolving the compound 1 in an organic solvent, and generating a compound 2 in the presence of a demethylating reagent;
s2, dissolving the compound 2 obtained in the step S1 in a solvent, carrying out Vilsmeie formylation reaction in the presence of an acylating agent and a catalyst, and treating after the reaction to obtain a compound 3;
s3, dissolving 2-methylquinoline and iodoethane in acetonitrile, heating the reaction solution to 85 ℃, stirring for reaction, cooling the reaction solution, precipitating with diethyl ether, and filtering to obtain a compound 4;
and S4, dissolving the compound 3 obtained in the step S2 and the compound 4 obtained in the step S3 in ethanol, adding a catalyst, heating and refluxing to perform enamine reaction, and treating after the reaction to obtain the colorimetric probe.
4. The method of making a colorimetric probe as claimed in claim 3, wherein the method of making comprises the steps of:
s1, dissolving the compound 1 in dichloromethane, dropwise adding a demethylating reagent boron tribromide under the ice-bath stirring condition, reacting at room temperature overnight, dropwise adding the reaction liquid into ice water after the reaction is finished, adjusting the pH to 6.0-8.0 by using a saturated sodium bicarbonate solution, drying and concentrating an organic phase after washing by using anhydrous sodium sulfate, and purifying a concentrated crude product by using column chromatography to obtain a compound 2;
s2, dissolving the compound 2 obtained in the step S1 in N, N-dimethylformamide, dropwise adding an N, N-dimethylformamide solution of phosphorus oxychloride under the condition of ice bath stirring, reacting for 2-3 hours, adding water, hydrolyzing for 2-3 hours, washing with water, drying and concentrating an organic phase through anhydrous sodium sulfate, and purifying a concentrated crude product through column chromatography to obtain a compound 3;
s3, dissolving 2-methylquinoline and iodoethane in acetonitrile, heating for reaction for a period of time, cooling with ice water, precipitating with diethyl ether, and filtering to obtain a compound 4;
s4, dissolving the compound 3 obtained in the step S2 and the compound 4 obtained in the step S3 in ethanol, adding a catalyst of pyrrolidine, heating and refluxing for reaction for a period of time, cooling to room temperature, concentrating, purifying a reaction crude product by column chromatography, and drying in vacuum to obtain the compound colorimetric probe.
5. The method for preparing a colorimetric probe as claimed in claim 4, wherein in step S1, the molar ratio of compound 1 to boron tribromide is 1mmol (15-25) mmol, the molar volume ratio of compound 1 to dichloromethane is 1mmol: (10-15) mL, the molar volume ratio of the compound 1 to the sodium bicarbonate solution is 1mmol: (4-6) mL.
6. The method for preparing a colorimetric probe as claimed in claim 4, wherein in the step S2, the molar ratio of the compound 2 to phosphorus oxychloride is 1mmol (2-4) mmol, the molar volume ratio of the compound 1 to N, N-dimethylformamide is 1mmol: (2-4) mL.
7. The method for preparing a colorimetric probe as claimed in claim 4, wherein in the step S3, the molar ratio of 2-methylquinoline to iodoethane is 1mmol (1.5-2.5) mmol, the molar volume ratio of 2-methylquinoline to acetonitrile is 1mmol: (5-10) mL, heating the reaction temperature to 80-85 ℃, and reacting for 18-24 hours.
8. The method for preparing a colorimetric probe as claimed in claim 4, wherein the molar ratio of the compound 3 to the compound 4 in the step S4 is 1mmol: (1.2-2) mmol, the molar volume ratio of the compound 3 to the tetrahydropyrrole is 1mmol: (0.1-0.3) mL, the molar volume ratio of the compound 4 to the ethanol is 1mmol: (10-15) mL, heating the reaction temperature to 80-85 ℃, and reacting for 8-12 hours.
9. Use of a colorimetric probe as claimed in claim 1 for the qualitative and quantitative analysis of trace amounts of water in a solvent.
10. The use of claim 9, wherein the colorimetric probe interacts with water molecules in the solvent in the presence of disodium phosphate to red-shift the wavelength of maximum ultraviolet absorption of the colorimetric probe.
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Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187884A (en) * | 2016-06-24 | 2016-12-07 | 贵州大学 | 2 [2 hydroxyl 5 (4 nitroazobenzene) styryl] 8 hydroxyquinoline colorimetric reagents and preparation and application |
| CN106987152A (en) * | 2017-03-08 | 2017-07-28 | 三峡大学 | One class fluorine boron near infrared fluorescent dye and the application in non-protonic solvent in the detection of minor amount of water |
| CN109456264A (en) * | 2018-11-30 | 2019-03-12 | 华南理工大学 | A kind of application of the fluorescence probe and preparation method thereof detecting nitroreductase with enzymatic reaction |
| CN110092752A (en) * | 2019-05-15 | 2019-08-06 | 三峡大学 | A kind of quinoline fluorescent chemicals, preparation method and applications |
| CN110117253A (en) * | 2018-02-05 | 2019-08-13 | 三峡大学 | A kind of organic fluorescent dye with piezallochromy characteristic, preparation method and applications |
| 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 |
| CN111607248A (en) * | 2020-06-04 | 2020-09-01 | 绍兴文理学院 | Quinoline type lyotropic color-changing fluorescent dye, preparation method thereof and application thereof in organic solvent water content measurement |
| CN111848509A (en) * | 2020-08-13 | 2020-10-30 | 江西科技师范大学 | Molecular rotor type red light mitochondrial probe and preparation method and application thereof |
| CN112645874A (en) * | 2020-12-24 | 2021-04-13 | 皖南医学院 | Lysosome targeted fluorescent probe and preparation method and application thereof |
| US20210109024A1 (en) * | 2019-10-11 | 2021-04-15 | The Hong Kong University Of Science And Technology | Single AIEgen for Multiple Tasks: Imaging of Dual Organelles and Evaluation of Cell Viability |
| CN112920113A (en) * | 2021-01-22 | 2021-06-08 | 华南理工大学 | Beta amyloid-targeted fluorescent probe, preparation method thereof and application thereof in Alzheimer's disease |
-
2022
- 2022-05-10 CN CN202210503722.3A patent/CN114989081B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187884A (en) * | 2016-06-24 | 2016-12-07 | 贵州大学 | 2 [2 hydroxyl 5 (4 nitroazobenzene) styryl] 8 hydroxyquinoline colorimetric reagents and preparation and application |
| CN106987152A (en) * | 2017-03-08 | 2017-07-28 | 三峡大学 | One class fluorine boron near infrared fluorescent dye and the application in non-protonic solvent in the detection of minor amount of water |
| CN110117253A (en) * | 2018-02-05 | 2019-08-13 | 三峡大学 | A kind of organic fluorescent dye with piezallochromy characteristic, preparation method and applications |
| CN109456264A (en) * | 2018-11-30 | 2019-03-12 | 华南理工大学 | A kind of application of the fluorescence probe and preparation method thereof detecting nitroreductase with enzymatic reaction |
| CN110092752A (en) * | 2019-05-15 | 2019-08-06 | 三峡大学 | A kind of quinoline fluorescent chemicals, preparation method and applications |
| US20210109024A1 (en) * | 2019-10-11 | 2021-04-15 | The Hong Kong University Of Science And Technology | Single AIEgen for Multiple Tasks: Imaging of Dual Organelles and Evaluation of Cell Viability |
| 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 |
| CN111607248A (en) * | 2020-06-04 | 2020-09-01 | 绍兴文理学院 | Quinoline type lyotropic color-changing fluorescent dye, preparation method thereof and application thereof in organic solvent water content measurement |
| CN111848509A (en) * | 2020-08-13 | 2020-10-30 | 江西科技师范大学 | Molecular rotor type red light mitochondrial probe and preparation method and application thereof |
| CN112645874A (en) * | 2020-12-24 | 2021-04-13 | 皖南医学院 | Lysosome targeted fluorescent probe and preparation method and application thereof |
| CN112920113A (en) * | 2021-01-22 | 2021-06-08 | 华南理工大学 | Beta amyloid-targeted fluorescent probe, preparation method thereof and application thereof in Alzheimer's disease |
Non-Patent Citations (1)
| Title |
|---|
| ZIXUAN ZHAO ET AL.: "A smartphone-available colorimetric and near-infrared fluorescence sensor for trace amounts of water detection in highly polar organic solvents", 《DYES AND PIGMENTS》 * |
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