CN114989081B - Colorimetric probe and preparation method and application thereof - Google Patents
Colorimetric probe and preparation method and application thereof Download PDFInfo
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- 238000010521 absorption reaction Methods 0.000 claims abstract description 17
- 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 12
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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
- 229940126214 compound 3 Drugs 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
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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
- G01N21/17—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
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- Y02P20/00—Technologies relating to chemical industry
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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, an intramolecular hydroxy group is used as a detection site, under the existence of disodium hydrogen phosphate, the maximum ultraviolet absorption wavelength of the colorimetric probe is subjected to red shift along with the increase of the water content of a solvent, the maximum ultraviolet absorption wavelength is enhanced in proportion along with the increase of the water content, the color change of the solution is larger, and the detection of trace water in the solvent is realized by monitoring the ultraviolet visible absorption spectrum change. 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 rapidly identified and can realize visual detection due to the fact that the color change of the colorimetric probe is visible to naked eyes, and has good potential application prospect. The colorimetric probe provided by the invention is simple in preparation method, easy to operate and convenient to popularize and apply.
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
Among many organic solvents, water is generally considered an impurity, and thus its measurement in solvents is of great importance for many industrial processes, food processing, biomedical and environmental monitoring, etc. For example, in chemistry, particularly in organometallic chemistry, the presence of water can cause the quenching of the reactive organometallic compounds, 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 accidents such as fires and explosions. In certain industrial processes, water plays a detrimental role, an example of which is petroleum-based fuels. The presence of water can lead to reduced engine performance, but more importantly, when the temperature is sufficiently low, emulsification and phase separation can occur, plugging the fuel lines, leading to engine damage and failure. Manufacturers of solvents and chemicals must ensure that their products have low moisture content to meet customer needs, etc.
Up to now, various methods have been used to determine water content, including karl fischer-tropsch (an. Chem.,1990,62,2504), flow analysis (FIA) (an. Chem.,1996,68,971), electrochemical and electro-physical sensing mechanisms (sens. Actioner a-Phys.,2005,118,202), and the like. However, most of these detection methods require complicated processes, complicated operations, expensive large-scale equipment, and long time. And is unfavorable for real-time on-site monitoring. In addition, colorimetric, fluorescent probes for the detection of water content in solvents have been reported in several journals, such as chem. ACS sustein.chem.eng., 2020,8,23,8857-8867; ACS Omega, 2019,4,10695-10701; 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.,2012,48,3933-3935; dye pigments, 2012,92,1199-1203; dye pigments 2011,88,307; org.biomol.chem.,2011, 9,1314; photochem.Photobiol.A-chem.,2011,222,52-55; sens.Actator B-chem.,2011,157,14-18, etc. However, these colorimetric and fluorescent probes have the disadvantages of long response time, low sensitivity, high detection limit, insignificant color change and the like, and these problems severely limit the practical application of these probes. Therefore, the development and operation are simple, the detection sensitivity is high, and the colorimetric probe with obvious color change is of great significance in the detection of trace water in an organic solvent.
Disclosure of Invention
The invention aims at providing a colorimetric probe, a preparation method and application thereof aiming at the defects of the prior art.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the first object of the invention is to provide a colorimetric probe, wherein the structural formula of the colorimetric probe is shown as formula I:
the second object of the present invention is to provide a method for preparing the colorimetric probe as described above, which comprises reacting 1 3-methoxytriphenylamine
The method is characterized by comprising the following steps of:
step S1, demethylating the compound 1 to obtain a compound 2, wherein the structural formula is as follows:
step S2, the compound 1 is subjected to Vilsmeie formylation reaction to generate a compound 3, and the structural formula is as follows:
step S3, carrying out alkylation reaction on 2-methylquinoline to obtain a compound 4, wherein the structural formula is as follows:
and S4, mixing the compound 3 and the compound 4, and reacting by using enamine to generate the colorimetric probe, wherein the structural formula of the colorimetric probe is shown in the formula I.
Further, the preparation method specifically comprises the following steps:
step S1, dissolving a compound 1 in an organic solvent, and generating a compound 2 in the presence of a demethylating reagent;
step S2, carrying out 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 the compound after the reaction to obtain a compound 3;
step S3, 2-methylquinoline and ethyl iodide are dissolved in acetonitrile, the reaction solution is heated to 85 ℃, stirred and reacted, the reaction solution is cooled and then precipitated by diethyl ether, and the compound 4 is obtained by filtration;
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.
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, regulating the pH value by using a saturated sodium bicarbonate solution, drying and concentrating an organic phase after water washing by using anhydrous sodium sulfate, and purifying a concentrated crude product by using 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 to hydrolyze for 2-3 hours, drying and concentrating an organic phase through anhydrous sodium sulfate after water washing, and purifying a concentrated crude product through column chromatography to obtain a compound 3;
step S3, 2-methylquinoline and ethyl iodide are dissolved in acetonitrile, after heating reaction is carried out for a period of time, ice water is cooled, diethyl ether is used for precipitation, and then the compound 4 is obtained by filtration;
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 of tetrahydropyrrole, heating and refluxing for reacting for a period of time, cooling to room temperature, concentrating, purifying a crude reaction product by column chromatography, and then 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), and the molar volume ratio of compound 1 to methylene chloride is 1mmol: (10-15) mL, molar volume ratio of compound 1 to sodium bicarbonate solution is 1mmol: (4-6) mL.
Further, in step S2, the molar ratio of the compound 2 to phosphorus oxychloride is 1mmol (2-4 mmol), and the molar volume ratio of the 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), and the molar volume ratio of 2-methylquinoline to acetonitrile is 1mmol: (5-10) mL, heating the reaction temperature to 80-85 ℃ and the reaction time to 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 compound 3 to tetrahydropyrrole is 1mmol: (0.1-0.3) mL, the molar volume ratio of compound 4 to ethanol is 1mmol: (10-15) mL, heating and reacting at 80-85 ℃ for 8-12 hours.
The third object of the invention is to provide the application of the colorimetric probe 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 red shifted.
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 fluorophore, an intramolecular hydroxy group is used as a detection site, under the existence of disodium hydrogen phosphate, the maximum ultraviolet absorption wavelength of the colorimetric probe is subjected to red shift along with the increase of the water content in a solvent, the ratio is enhanced along with the increase of the water content, the color change of the solution is larger, the detection of trace water in the solvent is realized by monitoring the change of an ultraviolet-visible absorption spectrum, the colorimetric probe can be used as a novel detection reagent for detecting trace water, the colorimetric and quantitative detection of trace water in the sample are performed, 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 is used for detecting trace water, can be rapidly identified, can be seen by naked eyes to change the color, and can realize visual detection;
(4) The colorimetric probe prepared by the invention can quickly respond to trace water in a solution, realizes dual-mode detection of spectrum and color comparison, does not need sample pretreatment, and has very simple detection;
(5) The colorimetric probe can provide a wider detection range, is applicable to various solvents such as DMSO, methanol, ethanol and the like, and has high sensitivity up to 100ppm.
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 spectrum of a colorimetric probe in example 1 of the present invention;
FIG. 3 is a mass spectrum of the colorimetric probe in example 1 of the present invention;
FIG. 4a is a chart showing the UV-visible absorption spectrum of a colorimetric probe prepared in example 1 for detecting trace amounts of water in a DMSO solution;
FIG. 4b is a graph of the ratio of absorption intensity of colorimetric probe in DMSO solution versus water content;
FIG. 5a is a chart showing the UV-visible absorbance spectra of colorimetric probes prepared in example 1 for detecting trace amounts of water in a methanol solution;
FIG. 5b is a graph of the ratio of absorption intensity of a colorimetric probe in methanol solution versus water content;
FIG. 6a is a chart showing the UV-visible absorbance spectra of colorimetric probes prepared in example 1 for detecting trace amounts of water in an ethanol solution;
FIG. 6b is a graph of the ratio of absorption intensity of a colorimetric probe in an ethanol solution versus water content;
FIG. 7 is a photograph showing the color change of the colorimetric probe prepared in example 1 in DMSO solution;
FIG. 8 is a photograph showing the color change of the colorimetric probe prepared in example 1 in methanol solution;
FIG. 9 is a photograph showing the 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, the following detailed description of the specific embodiments of the present invention will be given with reference to the accompanying drawings.
The structural formula of the colorimetric probe provided by the invention is shown as formula I, and the molecular formula is C 31 H 27 IN 2 O, the relative molecular weight of which is 570.46, is black purple solid powder and is dissolved in solvents such as DMSO, DMF, chloroform and the like.
The synthetic route of the colorimetric probe of the invention is as follows:
example 1
The preparation method of the colorimetric probe comprises the following steps:
step S1, 1.9g of compound 1 (3-methoxy triphenylamine) is dissolved in 10mL of dichloromethane, 10.1mL of boron tribromide is added dropwise by a syringe under the stirring of ice bath condition, the reaction is carried out at room temperature overnight, the reaction liquid is added into 100mL of ice water after the reaction is finished, the pH is regulated to be neutral by 24mL of saturated sodium bicarbonate solution, the organic phase is dried and concentrated by anhydrous sodium sulfate after three times of water washing, and the crude reaction product is purified by column chromatography to obtain 1.65g of compound 2 with the yield of 91.6%;
step S2, 783mg of compound 2 is dissolved in 6mL of N, N-dimethylformamide, under the condition of ice bath stirring, 6mmol of phosphorus oxychloride in N, N-dimethylformamide (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is added into the reaction liquid by injection, after reaction for 2 hours, water is added for hydrolysis for 2.5 hours, the organic phase is dried and concentrated by anhydrous sodium sulfate after washing with water for three times, and 687mg of pale green compound 3 is obtained by purifying the crude reaction product by column chromatography, and the yield is 79.2%.
Step S3, 1.43g of 2-methylquinoline and 2.34g of ethyl iodide are dissolved in acetonitrile, heated to 80 ℃ for reaction for 18 hours, cooled by ice water, precipitated by diethyl ether, and filtered to obtain 2.56g of black-red compound 4, wherein the yield is 85.6%;
step S4, 289mg of compound 3 and 358.8mg of compound 4 are dissolved in 10mL of ethanol, 100 mu L of tetrahydropyrrole is added, heating reflux is carried out for 8 hours at 80 ℃, cooling is carried out to room temperature, concentration is carried out, and the reaction crude product is purified by column chromatography to obtain 476mg of dark purple compound which is a colorimetric probe, and the yield is 83.5%.
The colorimetric probe obtained in example 1 was subjected to a structure confirmation study:
as shown in fig. 1, the nuclear magnetic resonance hydrogen spectrum of the colorimetric probe is structurally 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 nmr carbon spectrum of the colorimetric probe is structurally characterized by: 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 assist by high resolution mass spectrometry has demonstrated that HRMS (ESI) is m/z 444.2803[ M+H ]] + 。
Colorimetric probes of the invention, C 31 H 27 IN 2 O, chinese name: 2- [2- (4-diphenylamine-2-hydroxy-phenyl) -vinyl]-1-ethyl-quinoline salt iodide having a molecular weight of 570.46.
Successful synthesis of the colorimetric probe can be determined by nuclear magnetic resonance and mass spectrometry.
Example 2
The preparation method of the colorimetric probe comprises the following steps:
step S1, 1.9g of compound 1 (3-methoxy triphenylamine) is dissolved in 12mL of dichloromethane, 14.0mL of boron tribromide is added dropwise by a syringe under the stirring of ice bath condition, the reaction is carried out at room temperature overnight, the reaction liquid is added into 120mL of ice water after the reaction is finished, the pH is regulated to be neutral by 28mL of saturated sodium bicarbonate solution, the organic phase is dried and concentrated by using anhydrous sodium sulfate after three times of water washing, and the crude reaction product is purified by column chromatography to obtain 1.75g of compound 2 with the yield of 97.2%;
step S2, 783mg of compound 2 is dissolved in 8mL of N, N-dimethylformamide, 8mmol of phosphorus oxychloride in N, N-dimethylformamide (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is added dropwise to the reaction solution by injection under the condition of ice bath stirring, water is added for hydrolysis for 2.5h after reaction for 3h, an organic phase is dried and concentrated by anhydrous sodium sulfate after washing with water for three times, and 703mg of pale green compound 3 is obtained by purifying the crude reaction product by column chromatography, and the yield is 81.1%.
Step S3, 1.43g of 2-methylquinoline and 2.81g of ethyl iodide are dissolved in acetonitrile, heated to 82 ℃ for reaction for 20 hours, cooled by ice water, precipitated by diethyl ether, and filtered to obtain 2.47g of black-red compound 4, and the yield is 82.6%;
step S4, 289mg of compound 3 and 418.6mg of compound 4 are dissolved in 12mL of ethanol, 180 mu L of tetrahydropyrrole is added, heating reflux is carried out for 9 hours at 82 ℃, cooling is carried out to room temperature, concentration is carried out, and the crude reaction product is purified by column chromatography to obtain 458mg of dark purple compound which is a colorimetric probe, and the yield is 80.4%.
The colorimetric probe provided in example 2 was structurally characterized using the detection method provided in example 1, and the characterization results were identical to those in example 1, allowing for the successful synthesis of the colorimetric probe.
Example 3
The preparation method of the colorimetric probe comprises the following steps:
step S1, 1.9g of compound 1 (3-methoxy triphenylamine) is dissolved in 13mL of dichloromethane, 16.5mL of boron tribromide is added dropwise by a syringe under the stirring of ice bath condition, the reaction is carried out at room temperature overnight, the reaction liquid is added into 115mL of ice water after the reaction is finished, the pH is regulated to be neutral by 29mL of saturated sodium bicarbonate solution, the organic phase is dried and concentrated by anhydrous sodium sulfate after three times of water washing, and the crude reaction product is purified by column chromatography to obtain 1.63g of compound 2 with the yield of 90.5%;
step S2, 783mg of compound 2 is dissolved in 10mL of N, N-dimethylformamide, 10mmol of phosphorus oxychloride in N, N-dimethylformamide (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is dripped into the reaction solution by injection under the condition of ice bath stirring, water is added for hydrolysis for 2.5h after reaction for 3.5h, an organic phase is dried and concentrated by anhydrous sodium sulfate after washing with water for three times, and 722mg of pale green compound 3 is obtained by purifying a crude reaction product by column chromatography, and the yield is 83.3%.
Step S3, 1.43g of 2-methylquinoline and 3.41g of ethyl iodide are dissolved in acetonitrile, heated to 83 ℃ for reaction for 21 hours, cooled by ice water, precipitated by diethyl ether, and filtered to obtain 2.68g of black-red compound 4, and the yield is 89.6%;
step S4, 289mg of compound 3 and 308.3mg of compound 4 are dissolved in 14mL of ethanol, 240 mu L of tetrahydropyrrole is added, heating reflux is carried out for 10 hours at 83 ℃, cooling is carried out to room temperature, concentration is carried out, and the crude reaction product is purified by column chromatography to obtain 484mg of dark purple compound serving as a colorimetric probe, and the yield is 84.9%.
The colorimetric probe provided in example 3 was structurally characterized using the detection method provided in example 1, and the characterization results were identical to those in example 1, so that successful synthesis of the colorimetric probe could be determined.
Example 4
The preparation method of the colorimetric probe comprises the following steps:
step S1, 1.9g of compound 1 (3-methoxy triphenylamine) is dissolved in 15mL of dichloromethane, 19.5mL of boron tribromide is added dropwise by a syringe under the stirring of ice bath condition, the reaction is carried out at room temperature overnight, the reaction liquid is added into 140mL of ice water after the reaction is finished, the pH is regulated to be neutral by 32mL of saturated sodium bicarbonate solution, the organic phase is dried and concentrated by anhydrous sodium sulfate after three times of water washing, and the crude reaction product is purified by column chromatography to obtain 1.64g of compound 2 with the yield of 91.1%;
step S2, 783mg of compound 2 is dissolved in 12mL of N, N-dimethylformamide, 12mmol of phosphorus oxychloride in N, N-dimethylformamide (phosphorus oxychloride is dissolved in 3mL of N, N-dimethylformamide) is dripped into the reaction solution by injection under the condition of ice bath stirring, water is added for hydrolysis for 3.5h after reaction for 4.0h, an organic phase is dried and concentrated by anhydrous sodium sulfate after washing with water for three times, and 702mg of pale green compound 3 is obtained by purifying a crude reaction product by column chromatography, and the yield is 80.0%.
Step S3, 1.43g of 2-methylquinoline and 3.87g of ethyl iodide are dissolved in acetonitrile, heated to 85 ℃ for reaction for 24 hours, cooled by ice water, precipitated by diethyl ether, and filtered to obtain 2.67g of black-red compound 4, wherein the yield is 89.2%;
step S4, 289mg of compound 3 and 598.8mg of compound 4 are dissolved in 15mL of ethanol, 300 mu L of tetrahydropyrrole is added, heating reflux is carried out for 12 hours at 85 ℃, cooling is carried out to room temperature, concentration is carried out, and the crude reaction product is purified by column chromatography to obtain 488mg of dark purple compound which is a colorimetric probe, and the yield is 85.6%.
The colorimetric probe provided in example 4 was structurally characterized using the detection method provided in example 1, and the characterization results were identical to those in example 1, allowing for the successful synthesis of the colorimetric probe.
In order to demonstrate that the colorimetric probe of the present invention can be applied to qualitative and quantitative analysis of a trace amount of water in a solvent, the applicant conducted the following studies using the colorimetric probe prepared in example 1:
(1) Ultraviolet-visible absorption spectrum test of colorimetric probe in DMSO system
Different volumes of ultra-dry dimethyl sulfoxide solution are transferred into a cuvette containing auxiliary disodium hydrogen phosphate, 20 mu L of probe (1 mM) mother solution is added into the solution, the cuvette is uniformly shaken and placed, then different amounts of water are transferred into the cuvette and the total volume is 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% and 1%, respectively, and finally the cuvette is uniformly shaken and placed for 1 minute, and the ultraviolet-visible absorption spectrum change of the solution is recorded.
As shown in FIG. 4a, the test results showed that as the water content in the dimethyl sulfoxide solution increased, the absorption peak of the probe compound at 525nm gradually decreased, and a new absorption peak at 620nm appeared. The colorimetric probe can detect trace water in dimethyl sulfoxide by monitoring ultraviolet-visible absorption spectrum change.
As shown in FIG. 4b, the result shows 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 a good linear relationship, y=21.44x+0.09, R 2 ＝0.993。
(2) Ultraviolet-visible absorption spectrum test of colorimetric probe in methanol system
Different volumes of ultra-dry methanol solution are removed into a cuvette containing auxiliary disodium hydrogen phosphate, 20 mu L of probe (1 mM) mother solution is added into the solution, the cuvette is uniformly shaken and placed, then different amounts of water are removed into the cuvette and the total volume is 2mL, so that the water content (v/v) in the cuvette 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% and 10%, respectively, and finally the cuvette is uniformly shaken and placed for 1 minute, and the ultraviolet-visible absorption spectrum change of the solution is recorded.
As shown in FIG. 5a, the test results showed that the absorption peak of the probe compound at 530nm was gradually decreased with the increase of the water content in the methanol solution, and a new absorption peak was present at 585 nm. The colorimetric probe can detect trace water in methanol by monitoring ultraviolet visible absorption spectrum change.
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 a good linear relationship, y=0.76x+0.55, R 2 ＝0.993。
(3) Ultraviolet-visible absorption spectrum test of colorimetric probe in ethanol system
And transferring different volumes of ultra-dry ethanol solution into a cuvette containing auxiliary disodium hydrogen phosphate, adding 20 mu L of probe (1 mM) mother solution into the solution, shaking the cuvette evenly, standing, transferring different amounts of water into the cuvette and keeping the total volume of the cuvette to be 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%, 0.15%, 0.2%, 0.25%, 0.3%, 0.4%, 0.6%, 0.8% and 1%, shaking the cuvette evenly, standing for 1 minute, and recording the ultraviolet-visible absorption spectrum change of the solution before and after the reaction.
As shown in FIG. 6a, the test results showed that the absorption peak of the probe compound at 545nm was gradually decreased and a new absorption peak at 595nm was generated as the water content in the ethanol solution was increased. The colorimetric probe can detect trace water in ethanol by monitoring ultraviolet visible absorption spectrum change.
As shown in FIG. 6b, the results show that the ratio I of the water content to the absorption intensity of the probe detection system is in the range of 0-2.0% in the ethanol solution 595nm /I 545nm In a good linear relationship, y=5.21 x+0.94,R 2 ＝0.992。
(4) Detection of trace amounts of water in dimethyl sulfoxide solutions
Dissolving colorimetric probe in dimethyl sulfoxide solution to obtain a solution with concentration of 1×10 -3 The method comprises the steps of (1) transferring a solution of mol/L to a cuvette with disodium hydrogen phosphate, adding 60 mu L of probe mother solution into the solution, shaking the cuvette uniformly, transferring water with different contents into the cuvette and the total volume is 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% and 1%, respectively, and finally shaking the cuvette uniformly for 1 minute to record the color change of a solution system.
As shown in fig. 7, the test results show that the color of the solution changes from rose red to blue under natural light conditions with the increase of the water content in the dimethyl sulfoxide solution, which indicates that the colorimetric probe of the invention acts on water molecules in the dimethyl sulfoxide solution in the presence of the auxiliary disodium hydrogen phosphate and causes the color change of the solution.
(5) Detection of trace amounts of water in methanol solutions
Dissolving colorimetric probe in methanol to obtain a solution with concentration of 1×10 -3 And (3) removing different volumes of ultra-dry methanol solution from a mol/L solution, adding 60 mu L of probe mother solution into the solution, shaking the cuvette, standing, removing water with different contents into the cuvette and the total volume is 2mL, so that the water content (v/v) in the cuvette 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% and 10%, shaking the cuvette, standing for 1 minute, and recording the color change of a solution system.
As shown in fig. 8, the test results show that the color of the solution changes from purple to blue under natural light conditions as the water content of the methanol solution increases, indicating that the colorimetric probe of the present invention reacts with water molecules and causes a change in the color of the solution in the presence of the auxiliary disodium hydrogen phosphate in the methanol solution.
(6) Detection of trace amounts of water in ethanol solutions
Dissolving colorimetric probe in ethanol to obtain a solution with concentration of 1×10 -3 And (3) removing the solution of mol/L, namely removing the ultra-dry ethanol solution with different volumes into a cuvette with disodium hydrogen phosphate, adding 60 mu L of probe mother solution into the solution, shaking the cuvette evenly, standing, removing water with different contents into the cuvette and the total volume is 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%, 0.15%, 0.2%, 0.25%, 0.3%, 0.4%, 0.6%, 0.8% and 1%, shaking the cuvette evenly, standing for 1 minute, and recording the color change of a solution system.
As shown in fig. 9, the test results show that the color of the solution changes from blue-violet to blue under natural light conditions as the water content of the ethanol solution increases, indicating that the colorimetric probe of the present invention reacts with water molecules and causes a change in the color of the solution in the presence of the auxiliary disodium hydrogen phosphate in the ethanol solution.
The embodiments and features of the embodiments described herein may be combined with each other without conflict.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and principles of the invention are intended to be included within the scope of the invention.
Claims (10)
1. A colorimetric probe is characterized in that the structural formula of the colorimetric probe is shown as formula I
The illustration is:
2. A method for preparing a colorimetric probe as claimed in claim 1,
the preparation method adopts a compound 1 3-methoxy triphenylamine
As a starting material, comprising the steps of:
s1, demethylating the compound 1 to obtain a compound 2, wherein the structural formula is as follows:
s2, subjecting the compound 2 obtained in the step S1 to formylation reaction to generate a compound 3, wherein the structural formula is as follows:
and (3) carrying out alkylation reaction on the S3 and the 2-methylquinoline to obtain a compound 4, wherein the structural formula is as follows:
s4, mixing the compound 3 and the compound 4, and reacting by using enamine to generate the colorimetric probe, wherein the structural formula is shown in the formula I.
3. The method of preparing a colorimetric probe as claimed in claim 2, comprising the specific steps of:
s1, dissolving a 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 ethyl iodide in acetonitrile, heating the reaction solution to 80-85 ℃, stirring for reaction, cooling the reaction solution, 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, heating and refluxing to perform enamine reaction, and treating after the reaction to obtain the colorimetric probe.
4. A method of preparing a colorimetric probe as claimed in claim 3 comprising the specific steps of:
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 to 6.0-8.0 by using a saturated sodium bicarbonate solution, drying and concentrating an organic phase after water 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 to hydrolyze for 2-3 hours, drying and concentrating an organic phase after water washing by anhydrous sodium sulfate, and purifying a concentrated crude product by column chromatography to obtain a compound 3;
s3, dissolving 2-methylquinoline and ethyl iodide in acetonitrile, heating and reacting 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 tetrahydropyrrole, heating and refluxing for reacting for a period of time, cooling to room temperature, concentrating, purifying a crude reaction product by column chromatography, and vacuum drying to obtain the compound colorimetric probe.
5. The method of preparing a colorimetric probe according to claim 4, wherein in the step S1, the molar ratio of the compound 1 to boron tribromide is 1mmol (15-25 mmol), and the molar volume ratio of the compound 1 to methylene chloride is 1mmol: (10-15) mL, molar volume ratio of compound 1 to sodium bicarbonate solution is 1mmol: (4-6) mL.
6. The method of preparing a colorimetric probe according to claim 4, wherein in step S2, the molar ratio of the compound 2 to phosphorus oxychloride is 1mmol (2-4 mmol), and the molar volume ratio of the compound 1 to N, N-dimethylformamide is 1mmol: (2-4) mL.
7. The method of preparing a colorimetric probe according to claim 4, wherein in step S3, the molar ratio of 2-methylquinoline to iodoethane is 1mmol (1.5-2.5 mmol), and the molar volume ratio of 2-methylquinoline to acetonitrile is 1mmol: (5-10) mL, and the reaction time is 18-24 hours.
8. The method of preparing a colorimetric probe as claimed in claim 4, wherein in step S4, the molar ratio of compound 3 to compound 4 is 1mmol: (1.2-2) mmol, the molar volume ratio of compound 3 to tetrahydropyrrole is 1mmol: (0.1-0.3) mL, the molar volume ratio of compound 4 to ethanol is 1mmol: (10-15) mL, heating reaction temperature is 80-85 ℃ and reaction time is 8-12 hours.
9. Use of a colorimetric probe as claimed in claim 1 for qualitative and quantitative analysis of trace amounts of water in a solvent.
10. The use of claim 9, wherein the colorimetric probe reacts with water molecules in the solvent in the presence of disodium hydrogen phosphate such that the maximum ultraviolet absorption wavelength of the colorimetric probe is red shifted.
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