CN117384099A - A ratiometric colorimetric fluorescent probe and its preparation method and application - Google Patents
A ratiometric colorimetric fluorescent probe and its preparation method and application Download PDFInfo
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- CN117384099A CN117384099A CN202310782768.8A CN202310782768A CN117384099A CN 117384099 A CN117384099 A CN 117384099A CN 202310782768 A CN202310782768 A CN 202310782768A CN 117384099 A CN117384099 A CN 117384099A
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Abstract
本发明属于草酰氯检测技术领域，公开了一种比率比色荧光探针及其制备方法和应用，所述比率比色荧光探针为2‑(2‑羟基‑4‑甲氧基苯基)‑1H‑蒽[1,2‑d]咪唑‑6,11‑二酮，简写为PMD，其化学结构式为：该荧光探针是将1,2‑二氨基蒽醌和2‑羟基‑4‑甲氧基苯甲醛，在催化剂条件下反应合成。本发明的PMD的乙腈溶液呈现出红色且发出红色的荧光，在与草酰氯接触后溶液变为黄色，并且荧光呈现出黄色，能实现对样品内草酰氯的灵敏定量检测，具有操作简便，成本低廉，响应灵敏，易于推广和应用等优点。
The invention belongs to the technical field of oxalyl chloride detection and discloses a ratiometric colorimetric fluorescent probe and its preparation method and application. The ratiometric colorimetric fluorescent probe is 2-(2-hydroxy-4-methoxyphenyl) ‑1H‑Anthracene[1,2‑d]imidazole‑6,11‑dione, abbreviated as PMD, its chemical structural formula is: The fluorescent probe is synthesized by reacting 1,2-diaminanthraquinone and 2-hydroxy-4-methoxybenzaldehyde under catalyst conditions. The acetonitrile solution of PMD of the present invention appears red and emits red fluorescence. After contacting with oxalyl chloride, the solution turns yellow and the fluorescence appears yellow. It can realize sensitive and quantitative detection of oxalyl chloride in the sample and has the advantages of simple operation and low cost. It has the advantages of low cost, responsiveness, and easy promotion and application.
Description
Technical Field
The invention belongs to the technical field of oxalyl chloride detection, and particularly relates to a ratio colorimetric fluorescent probe and a preparation method and application thereof.
Background
Oxalyl chloride is a synthetic intermediate of medicines, pesticides, coatings and the like, is used as a raw material for synthesizing antibiotics in the aspect of medicines, is used as a raw material for synthesizing methyl acrylamide isocyanate in the aspect of coatings, and is widely used in the pesticide industry for synthesizing super-efficient sulfonylurea herbicides such as benzsulfuron, plant growth regulators and the like. However, oxalyl chloride is extremely toxic and can severely irritate the eyes, burn the skin and mucous membranes. Oxalyl chloride inhalation toxicology studies indicate that acute bronchitis, alveolar exudates and obstruction can occur after 1 hour of exposure to oxalyl chloride at a concentration of 1232 ppm. The inhaled oxalyl chloride also reacts strongly with water in the respiratory tract, releasing toxic gases: carbon monoxide and hydrogen chloride. Therefore, a sensitive, accurate and convenient oxalyl chloride monitoring method is critical for maintaining production and public health safety.
At present, gas chromatography-mass spectrometry combination, electrochemical sensors and the like are adopted at home and abroad, but the instruments are expensive, have large volume and are not easy to move; and the method has the defects of long test analysis time, multiple factors to be interfered and the like. The fluorescence detection has excellent detection sensitivity and selectivity, and the operation method is simple and suitable for detecting the sample to be detected in real time. However, few reports on the fluorescent probe of oxalyl chloride are at home and abroad at present, and the design of the fluorescent probe with low cost, rapid and sensitive detection and simple test method has very important significance.
Disclosure of Invention
In order to solve the above-mentioned disadvantages and drawbacks of the prior art, a primary object of the present invention is to provide a ratio colorimetric fluorescent probe.
It is another object of the present invention to provide a method for preparing the ratio colorimetric fluorescent probe.
It is still another object of the present invention to provide the use of the above ratio colorimetric fluorescent probe, by which an extremely small amount (as low as 0.0053. Mu. Mol/L) of oxalyl chloride in a sample can be quantitatively detected.
The aim of the invention is achieved by the following technical scheme:
a ratio colorimetric fluorescent probe which is 2- (2-hydroxy-4-methoxyphenyl) -1H-anthracene [1,2-d ] imidazole-6, 11-dione and has a chemical structural formula:
the preparation method of the ratio colorimetric fluorescent probe comprises the following steps:
under the existence of a catalyst, 1, 2-diaminoanthraquinone and 2-hydroxy-4-methoxybenzaldehyde are dissolved in an organic solvent and uniformly mixed, and the mixture reacts at 60 to 90 ℃ to obtain 2- (2-hydroxy-4-methoxyphenyl) -1H-anthracene [1,2-d ] imidazole-6, 11-dione, namely the ratio colorimetric fluorescent probe.
Preferably, the catalyst is trifluoroacetic acid, the molar ratio of the 1, 2-diaminoanthraquinone to the 2-hydroxy-4-methoxybenzaldehyde is 1 (1-1.2), the reaction time is 4-8 h, and the organic solvent is ethanol or methanol.
The ratio colorimetric fluorescent probe is applied to detection of oxalyl chloride.
Preferably, the ratio colorimetric fluorescent probe comprises the following specific steps when detecting oxalyl chloride:
s1, adding the fluorescent probes of claim 1 into acetonitrile solution of oxalyl chloride, and preparing at least 8 different standard solutions containing the fluorescent probes;
s2, respectively measuring fluorescence emission spectrums of the standard solutions, wherein the excitation wavelength is 400nm, oxalyl chloride is taken as an abscissa, and the ratio of fluorescence emission peak intensities of the standard solutions at the wavelength of 527nm and 617nm is taken as an ordinate, so as to establish a standard curve;
s3, adding a fluorescent probe into the sample to be detected, controlling the concentration of the fluorescent probe to be equal to that of the fluorescent probe in the standard solution, measuring the fluorescence emission spectrum of the fluorescent probe under the excitation light with the excitation wavelength of 400nm, and calculating the oxalyl chloride content of the sample to be detected according to the standard curve.
Preferably, the concentration of the fluorescent probe in the standard solution in the step S1 is 1-10 mu M; the content of oxalyl chloride in the standard solution is 0.1-1 mM.
The fluorescent probe is applied to the preparation of test paper for detecting oxalyl chloride in air.
Compared with the prior art, the invention has the following beneficial effects:
1. the ratio colorimetric fluorescent probe is red solid powder, has good optical stability, has a linear relation to the concentration of oxalyl chloride, and can be used for accurately measuring the oxalyl chloride.
2. The ratio colorimetric fluorescent probe is an anthraquinone-based colorimetric ratio fluorescent probe, has good response to an acetonitrile solution of oxalyl chloride, is sensitive to the concentration of the oxalyl chloride, changes the fluorescence of an aqueous solution thereof from red to yellow under an ultraviolet lamp along with the increase of the concentration of the oxalyl chloride, and changes the aqueous solution thereof from red to yellow under sunlight. The method can realize sensitive and quantitative detection of oxalyl chloride in the sample, and has the advantages of simple operation, low cost, sensitive response, easy popularization and application and the like.
Drawings
FIG. 1 is a synthetic route diagram of PMD of fluorescent probe of example 1;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the PMD of the fluorescent probe of example 1;
FIG. 3 is a mass spectrum of the PMD of the fluorescent probe of example 1;
FIG. 4 is a plot of fluorescence emission spectra of the fluorescent probe PMD of example 2 reacted with varying concentrations of oxalyl chloride in acetonitrile solution versus fit;
FIG. 5 is an ultraviolet absorbance spectrum of a fluorescent probe PMD of example 2 reacted with oxalyl chloride in acetonitrile solution;
FIG. 6 is a photograph of the color response of the fluorescent probe PMD of example 2 to oxalyl chloride acetonitrile solution;
FIG. 7 is a photograph of the fluorescence response of the fluorescent probe PMD of example 2 to oxalyl chloride acetonitrile solution;
FIG. 8 is a fluorescence emission spectrum of the fluorescent probe PMD of example 3 for reaction of various interfering species;
FIG. 9 is the color of the test paper obtained in example 4, which is observed under natural light and ultraviolet light.
Detailed Description
The present invention is further illustrated below in conjunction with specific examples, but should not be construed as limiting the invention. The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
EXAMPLE 1 Synthesis of Compound PMD
In the presence of trifluoroacetic acid as a catalyst, adding 40mL of absolute ethyl alcohol into 1, 2-diaminoanthraquinone and 2-hydroxy-4-methoxybenzaldehyde, carrying out reflux reaction for 6H at 70 ℃ under the protection of nitrogen, cooling in an ice bath at 0 ℃ after the reaction is finished, filtering, washing excessive impurities with ethanol, drying the obtained solid, purifying the obtained solid by a silica gel chromatographic column (methylene dichloride), and putting the obtained product into a vacuum drying oven for drying at 50 ℃ for 24H to obtain 350mg of red solid powder compound 2- (2-hydroxy-4-methoxyphenyl) -1H-anthracene [1,2-d ] imidazole-6, 11-dione (PMD), wherein the yield is 49 percent, and the synthetic route is shown in figure 1.
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the PMD of the fluorescent probe of example 1. As can be seen from the view of figure 2, 1 h NMR (600 MHz, chloroform-d) δ11.51 (s, 1H), 9.74 (s, 1H), 8.61 (s, 1H), 8.34 (d, J=7.8 Hz, 1H), 8.31-8.28 (m, 1H), 7.83-7.69 (m, 3H), 7.37 (d, J=8.5 Hz, 1H), 6.60-6.56 (m, 2H), 3.90 (s, 3H) demonstrated the desired product. FIG. 3 is a mass spectrum of the fluorescent probe PMD of example 1. The mass spectrum is used for auxiliary demonstration, and the method specifically comprises the following steps: MS (ESI) m/z=371.104 [ M+H ]] + . The synthesized product can be determined to be the PMD of a fluorescent probe by analysis, and the molecular formula of the probe is C 22 H 14 N 2 O 4 。
Example 2 spectral response of Compound PMD to oxalyl chloride in solution
Prepare a test stock solution of acetonitrile of fluorescent probe PMD at a concentration of 1mM for use. 30. Mu.L of this mother solution was measured and added dropwise to acetonitrile solutions of 0. Mu.M, 1. Mu.M, 2. Mu.M, 3. Mu.M, 4. Mu.M, 5. Mu.M, 6. Mu.M, 7. Mu.M, 8. Mu.M, 9. Mu.M, and 10. Mu.M oxalyl chloride, respectively, and the volumes were fixed to 3mL with the corresponding acetonitrile solutions so that the probe concentration in the test solution was 10.0. Mu.M and the oxalyl chloride concentration was 0 to 10. Mu.M, and fluorescence spectrum test was performed. And establishing a standard curve of the fluorescence intensity and the phosgene concentration according to the fluorescence intensity in each system. FIG. 4 is a plot of fluorescence emission spectra versus fit for the fluorescent probe PMD of example 2 reacted with varying concentrations of oxalyl chloride in acetonitrile solution. Wherein, (a) is a fluorescence spectrum, and (b) is a fitted curve of the fluorescence spectrum. As can be seen from fig. 4, the wavelength blue shifts from 617nm to 527nm with increasing concentration of oxalyl chloride, and has a good linear relationship. FIG. 5 is an ultraviolet absorbance spectrum of the fluorescent probe PMD of example 2 reacted with oxalyl chloride in acetonitrile solution. FIG. 6 is a photograph of the color response of the fluorescent probe PMD of example 2 to oxalyl chloride acetonitrile solution; as can be seen from FIG. 6, the fluorescence changed from red to yellow upon addition of oxalyl chloride. FIG. 7 is a photograph of the fluorescence response of the fluorescent probe PMD of example 2 to oxalyl chloride acetonitrile solution. As can be seen from FIG. 7, the color of the solution changed from red to yellow upon addition of oxalyl chloride.
Sensitivity of fluorescent probe PMD to detect oxalyl chloride: adding different amounts of oxalyl chloride into 10 mu M fluorescent probe solution, and recording the fluorescence emission intensity ratio F of the reaction solution system at 527nm and 617nm by using a fluorescence spectrum under the conditions that the excitation wavelength of the fluorescent probe is 400nm and the reaction time is 60s by using the oxalyl chloride concentration as an abscissa 527 /F 617 nm is the ordinate, and a correction curve is drawn. The regression curve of oxalyl chloride in the low concentration range is shown in fig. 4 (b), and the regression curve is: y=0.00388+k×x (r=0.99); wherein y is the fluorescence intensity ratio F of the fluorescent probe at 527nm to 617nm 527 /F 617 X is oxalyl chloride concentration, k= 0.2659.
Detection limit lod=3×s.d./K, where K is the slope of the curve equation and s.d. represents the fluorescence intensity ratio F of the probe without oxalyl chloride 527 /F 617 nm standard deviation. LOD=3× 0.000472 +. 0.2659 =0.0053. Mu. Mol/L, from which it can be seen that the fluorescent probe of the invention detects oxalyl chlorideIs higher.
Example 3 selectivity to different common Compounds
A test stock solution of acetonitrile solution of the fluorescent probe PMD at a concentration of 1mM was prepared for use. Formaldehyde (HClO) and phosgene (COCl) were prepared at a concentration of 10mM 2 ) Hydrogen peroxide (H) 2 O 2 ) Phenol (C) 6 H 5 OH), isocyanate (CHNO), hydrazine (NH) 2 NH 2 ) Benzenesulfonyl chloride (C) 6 H 5 ClO 2 S), acetylacetone (C) 5 H 8 O 2 ) Benzene (C) 6 H 6 ) Oxalyl chloride (C) 3 Cl6O 3 ) Carbon disulphide (CS) 2 ) Styrene (C) 8 H 8 ) Toluene (C) 7 H 8 ). And (3) measuring 100 mu L of the mother solution, respectively dripping the mother solutions into acetonitrile solutions of different small molecules to be detected, and using the corresponding acetonitrile solutions to fix the volume to 10mL so that the concentration of the probe in the test solution is 10.0 mu M, and performing fluorescence detection when the concentration of the small molecules to be detected is 10.0 mu M. FIG. 8 is a fluorescence emission spectrum of the fluorescent probe PMD of example 3 for reaction of various interfering species. As can be seen in FIG. 8, the probe PMD only shows a blue shift in the presence of oxalyl chloride.
Example 4 detection of oxalyl chloride by fluorescent test paper
10mg PMD is dissolved in 20mL, then 100mg trimethylolpropane triglycidyl ether is added, the mixture is stirred for 30min by a magnetic stirrer, and then the solution of the fluorescent probe PMD is uniformly loaded on the cut clean filter paper to prepare the fluorescent detection test paper for detecting oxalyl chloride. FIG. 9 is the color of the test paper obtained in example 4, which is observed under natural light and ultraviolet light. Wherein, (a) is observed under natural light, and (b) is observed under ultraviolet light. (a) Blank, probe PMD plus oxalyl chloride in sequence from left to right, (b) blank, probe PMD plus oxalyl chloride in sequence from left to right. As shown in FIG. 9, the test paper changed color from pink to yellow under sunlight, and from orange to yellow under irradiation of 365nm ultraviolet lamp. Therefore, the oxalyl chloride in the air can be detected rapidly, efficiently and simply.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (7)
1. A ratio colorimetric fluorescent probe is characterized by being 2- (2-hydroxy-4-methoxyphenyl) -1H-anthracene [1,2-d ] imidazole-6, 11-dione, and the chemical structural formula is as follows:
2. the method for preparing the ratiometric colorimetric fluorescent probe according to claim 1, comprising the steps of:
under the existence of a catalyst, 1, 2-diaminoanthraquinone and 2-hydroxy-4-methoxybenzaldehyde are dissolved in an organic solvent and uniformly mixed, and the mixture reacts at 60 to 90 ℃ to obtain 2- (2-hydroxy-4-methoxyphenyl) -1H-anthracene [1,2-d ] imidazole-6, 11-dione, namely the ratio colorimetric fluorescent probe.
3. The method for preparing the colorimetric fluorescent probe according to claim 2, wherein the catalyst is trifluoroacetic acid, the molar ratio of the 1, 2-diaminoanthraquinone to the 2-hydroxy-4-methoxybenzaldehyde is 1 (1-1.2), the reaction time is 4-8 hours, and the organic solvent is ethanol or methanol.
4. Use of the ratiometric colorimetric fluorescent probe of claim 1 for detecting oxalyl chloride.
5. The use of a ratiometric colorimetric fluorescence probe according to claim 4 for detecting oxalyl chloride, comprising the specific steps of:
s1, adding the fluorescent probes of claim 1 into acetonitrile solution of oxalyl chloride, and preparing at least 8 different standard solutions containing the fluorescent probes;
s2, respectively measuring fluorescence emission spectrums of the standard solutions, wherein the excitation wavelength is 400nm, oxalyl chloride is taken as an abscissa, and the ratio of fluorescence emission peak intensities of the standard solutions at the wavelength of 527nm and 617nm is taken as an ordinate, so as to establish a standard curve;
s3, adding a fluorescent probe into the sample to be detected, controlling the concentration of the fluorescent probe to be equal to that of the fluorescent probe in the standard solution, measuring the fluorescence emission spectrum of the fluorescent probe under the excitation light with the excitation wavelength of 400nm, and calculating the oxalyl chloride content of the sample to be detected according to the standard curve.
6. The use of a ratiometric colorimetric fluorescent probe for detecting oxalyl chloride according to claim 5, wherein the concentration of the fluorescent probe in the standard solution in step S1 is 1-10 μm; the content of oxalyl chloride in the standard solution is 0.1-1 mM.
7. Use of the fluorescent probe according to claim 1 for preparing test paper for detecting oxalyl chloride in air.
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Citations (4)
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|---|---|---|---|---|
| US20090253707A1 (en) * | 2008-04-02 | 2009-10-08 | National Defense Medical Center | Heteroannelated anthraquinone derivatives and the synthesis method thereof |
| CN106045878A (en) * | 2016-05-12 | 2016-10-26 | 山西大学 | A kind of anthraquinone derivative and its synthesis method and application in detecting Cu2+ |
| CN109096203A (en) * | 2018-08-30 | 2018-12-28 | 河南省农业科学院农业质量标准与检测技术研究所 | A kind of mercury ion fluorescence probe and its preparation method and application based on anthraquinone derivative |
| CN111777575A (en) * | 2020-07-13 | 2020-10-16 | 江苏师范大学 | A high-sensitivity fluorescent probe for detecting oxalyl chloride and its preparation method and application |
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Patent Citations (4)
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| US20090253707A1 (en) * | 2008-04-02 | 2009-10-08 | National Defense Medical Center | Heteroannelated anthraquinone derivatives and the synthesis method thereof |
| CN106045878A (en) * | 2016-05-12 | 2016-10-26 | 山西大学 | A kind of anthraquinone derivative and its synthesis method and application in detecting Cu2+ |
| CN109096203A (en) * | 2018-08-30 | 2018-12-28 | 河南省农业科学院农业质量标准与检测技术研究所 | A kind of mercury ion fluorescence probe and its preparation method and application based on anthraquinone derivative |
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