Colorimetric fluorescent probe for visual real-time detection of dichloromethane
By developing a colorimetric fluorescent probe that visualizes real-time identification of dichloromethane, the problem of complex and inability to detect dichloromethane in the prior art is solved, and a fast, accurate and visual detection effect is achieved.
Patent Information
- Application Number
- CN202311689079.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-12-08
- Publication Date
- 2025-06-17
AI Technical Summary
The prior art has problems in dichloromethane detection, such as large equipment, professional operators, and inability to conduct real-time on-site inspection, which is difficult to meet the needs of rapid monitoring and rapid response.
Develop a colorimetric fluorescent probe that visualizes real-time identification of dichloromethane to achieve fast and accurate dichloromethane detection through naked-eye colorimetric and ultraviolet lamp irradiation.
The rapid, accurate and visual detection of dichloromethane is achieved, which overcomes the equipment complexity and operation difficulty of traditional methods, and improves the detection timeliness.
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Figure CN120157653A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of inspection and testing, and particularly to a colorimetric fluorescent probe for visual and real-time identification of dichloromethane. Technical Background
[0002] Dichloromethane, abbreviated as DCM, is a member of the chloromethane family. It is a transparent and volatile liquid, colorless, slightly soluble in water, and readily soluble in organic solvents. Unfortunately, this compound is toxic to living organisms and is thus classified as a Group 2 carcinogen. More than 1 million tons of dichloromethane are generated annually by global industrial activities, and it is widely used in chemical synthesis, purification, and cleaning processes in fields such as aerospace, electronics, and medicine. Although dichloromethane can rapidly dissolve organic substances, its toxic nature makes it a highly dangerous substance.
[0003] The main ways for humans to be exposed to dichloromethane include inhalation, skin contact, and ingestion. Due to its presence in the air, inhalation is the main exposure route. Exposure to dichloromethane may cause symptoms such as dizziness, nausea, and vomiting, and may even lead to ataxia, loss of consciousness, and death at high concentrations.
[0004] In recent years, more attention has been paid to the environmental and health hazards of dichloromethane. At the same time, the involvement of the chloromethane family in cases of unnatural death has also raised widespread social concerns. In the past, dichloromethane was used as an anesthetic and sedative, but with its extensive application in the medical and industrial fields, its hazards to human health and the environment have gradually emerged. These health risks have led to an urgent need for detection and monitoring methods.
[0005] Currently, gas chromatography-mass spectrometry (GC-MS) technology is applied to the qualitative and quantitative detection of dichloromethane. Although GC-MS technology performs well in terms of accuracy and sensitivity, its characteristics such as large equipment size, the need for trained operators, and the inability to perform real-time on-site detection limit its convenience in practical applications. Therefore, in order to meet the requirements of rapid monitoring and quick response, it is particularly important to develop a method for the identification of dichloromethane that is rapid, accurate, and visible to the naked eye. Summary of the Invention
[0006] The purpose of the present invention is to provide a colorimetric fluorescent probe for visual and real-time identification of dichloromethane, which can achieve on-site visual and rapid detection of dichloromethane and improve the timeliness of dichloromethane detection.
[0007] The structural formula of a colorimetric fluorescent probe for visual and real-time detection of dichloromethane according to the present invention is:
[0008]
[0009] The application of the above-mentioned colorimetric fluorescent probe for visual and real-time detection of dichloromethane is to use the colorimetric fluorescent probe for visual and real-time detection of dichloromethane to detect whether an unknown reagent is dichloromethane.
[0010] The method for qualitatively detecting whether a solution is dichloromethane by naked-eye colorimetry using a colorimetric fluorescent probe for visual and real-time detection of dichloromethane is carried out according to the following steps:
[0011] I. Dissolve the colorimetric fluorescent probe for visual and real-time detection of hypochlorous acid in organic solvent III to prepare a probe stock solution A;
[0012] II. Dilute the probe stock solution A obtained in step I with different solvents to obtain a probe solution B;
[0013] III. Irradiate the probe solution B with a handheld ultraviolet lamp, and the probe solution shows a bright blue color;
[0014] IV. Add the probe solution A obtained in step I to the unknown solvent to obtain a test solution C;
[0015] V. After standing the probe solution C for 30 seconds, irradiate the test solution C with a handheld ultraviolet lamp. If the test solution C shows a dark purple color and weak fluorescence, it is determined that the solution to be tested mainly contains dichloromethane;
[0016] The concentration of the colorimetric fluorescent probe for visual and real-time detection of dichloromethane in step I is 1 mmol·L –1 .
[0017] The organic solvent III in step I is methanol, dimethyl sulfoxide, DMF, acetonitrile, acetone, ethyl acetate, tetrahydrofuran, toluene, chloroform, and carbon tetrachloride.
[0018] The solvents in step II are methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, acetone, ethyl acetate, tetrahydrofuran, toluene, chloroform, carbon tetrachloride, and phosphate buffer solution.
[0019] The concentration of the colorimetric fluorescent probe for naked-eye and real-time detection of dichloromethane in the probe solution B in step II is 0.01 - 0.05 mmol·L –1 .
[0020] The concentration of the PBS solution in step II is 0.01 mol·L –1 , pH = 7.40.
[0021] The method for qualitatively detecting dichloromethane in a solution by ultraviolet and fluorescence methods using the colorimetric fluorescent probe for visual and real-time detection of dichloromethane prepared in this example is carried out according to the following steps:
[0022] 1. Dissolve the colorimetric fluorescent probe for visualizing and real-time detecting dichloromethane in water-miscible methanol to prepare a probe stock solution A with a concentration of 1 mmol·L –1 Probe stock solution A;
[0023] 2. Dilute the probe stock solution A obtained in step 1 with different solvents to obtain a probe solution B;
[0024] 3. Add the probe solution A obtained in step 1 to dichloromethane to obtain a test solution C;
[0025] 4. After the probe solution B and the test solution C are placed at room temperature for 30 seconds, measure the ultraviolet absorption spectral results of each test solution as Figure 4 shown. Measure the fluorescence emission spectra of each test solution at an excitation wavelength of 330 nm and an excitation slit width of 5.0 nm, and the results are as Figure 5 shown.
[0026] Advantages and beneficial effects of the present invention:
[0027] We innovatively synthesized a unique fluorescent probe for dichloromethane, which is based on a specific molecular structure and will generate ultraviolet and fluorescent signals different from other solvents in the presence of dichloromethane. This probe can not only quickly visualize and identify dichloromethane, but also has high selectivity and sensitivity, overcoming many limitations in traditional methods. Its low cost and easy-to-use characteristics enable it to be widely applied to various laboratory and on-site scenarios, providing an efficient and reliable solution for safety monitoring and environmental protection. Description of the drawings
[0028] Figure 1 It is a diagram of the color change of the probe solution and after adding dichloromethane
[0029] Figure 2 It is the NMR spectrum of the dichloromethane probe
[0030] Figure 3 It is the mass spectrum of the dichloromethane probe
[0031] Figure 4 It is the ultraviolet absorption spectra of the dichloromethane probe in different solvents
[0032] Figure 5 It is the fluorescence emission spectra of the dichloromethane probe in different solvents Examples
[0033] Verify the beneficial effects of the present invention with the following examples.
[0034] In this example, a colorimetric fluorescent probe for visualizing and real-time detecting dichloromethane was prepared.
[0035] It was characterized by nuclear magnetic resonance spectroscopy and mass spectrometry, and the results obtained were as Figure 2 and 3 .
[0036] I. Dissolve the colorimetric fluorescent probe for visual real-time detection of dichloromethane in water-miscible methanol to prepare a probe stock solution A with a concentration of 1 mmol·L –1 ;
[0037] II. Dilute the probe stock solution A with methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, acetone, ethyl acetate, tetrahydrofuran, toluene, chloroform, carbon tetrachloride and phosphate buffer solution respectively to prepare a fluorescent probe solution B with a concentration of 1.0×10 -5 mol / L;
[0038] III. Add the probe stock solution A to dichloromethane to prepare a fluorescent probe solution C with a concentration of 1.0×10 -5 mol / L;
[0039] IV. After the test solution C is placed at room temperature for 30 seconds, irradiate the probe solution B and the test solution C with a handheld ultraviolet lamp respectively. The probe solution B shows bright green, and the test solution C shows dark blue, as Figure 1 shown.
[0040] This indicates that in the presence of dichloromethane, the ultraviolet absorption, emission wavelength and emission intensity of the colorimetric fluorescent probe for visual real-time detection of dichloromethane have all changed, and the purpose of qualitative detection of dichloromethane by naked-eye colorimetry of the colorimetric fluorescent probe for visual real-time detection of dichloromethane can be achieved.
[0041] The method for qualitative detection of dichloromethane by ultraviolet and fluorescence methods using the colorimetric fluorescent probe for visual real-time detection of dichloromethane prepared in this example is carried out according to the following steps:
[0042] I. Dissolve the colorimetric fluorescent probe for visual real-time detection of dichloromethane in water-miscible dimethyl sulfoxide to prepare a probe stock solution A with a concentration of 1 mmol·L –1 ;
[0043] II. Dilute the probe stock solution A obtained in step I with methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, acetone, ethyl acetate, tetrahydrofuran, toluene, chloroform, carbon tetrachloride and phosphate buffer solution respectively to prepare a fluorescent probe solution B with a concentration of 1.0×10 -5 mol / L;
[0044] III. Add the probe solution A obtained in step I to dichloromethane to obtain a test solution C with a concentration of 1.0×10 -5 mol / L;
[0045] IV. After the probe solution B and the test solution C were left at room temperature for 30 seconds, the ultraviolet absorption spectra of each test solution were measured as follows Figure 4 shown. The fluorescence emission spectra of each test solution were measured at an excitation wavelength of 330 nm and an excitation slit width of 5.0 nm, and the results are as follows Figure 5 shown.
[0046] It can be seen from Figure 4 that the ultraviolet absorption spectrum of the dichloromethane probe solution C is very different from that of the probe solution B, and there is a specific broad peak at 600 nm, so the dichloromethane can be qualitatively determined. It can be seen from Figure 5 that the fluorescence emission wavelength of the fluorescence probe solution B is about 490 nm, and the fluorescence intensity is 450 - 600 a.u. The fluorescence intensity of the solution C prepared with dichloromethane is reduced to 75 a.u., and the quenching at 490 nm reaches 1 / 8 of the fluorescence intensity of the fluorescence probe solution. Therefore, it can be determined from the fluorescence emission spectrum that the fluorescence probe solution has a selective recognition property for dichloromethane.
Claims
1. A colorimetric fluorescent probe for visual identification of dichloromethane, and the structural formula of the fluorescent probe is:
2. The colorimetric fluorescent probe for visual detection of dichloromethane according to claim 1, wherein Visual differentiation is used to distinguish dichloromethane from other common solvents, providing a new method for the identification of dichloromethane, which is carried out according to the following steps:
1. Dissolve the colorimetric fluorescence probe for detecting dichloromethane in organic solvent III to prepare a probe stock solution A; 2. Dilute the probe stock solution A obtained in step 1 with different solvents to obtain a probe solution B; 3. Irradiate the probe solution B with a handheld ultraviolet lamp, and the probe solution shows a bright blue color; 4. Add the probe solution A obtained in step 1 to the organic solvent to be tested to obtain a test solution C; 5. After standing the probe solution C for 30 seconds, irradiate the test solution C with a handheld ultraviolet lamp. If the test solution C shows a dark purple color and weak fluorescence, it is determined that the solution to be tested is dichloromethane.
3. The colorimetric fluorescent probe for visual identification of dichloromethane according to claim 1, wherein The colorimetric fluorescence probe prepared in this example is used for qualitative detection of dichloromethane by ultraviolet and fluorescence methods, which is carried out according to the following steps:
1. Dissolve the colorimetric fluorescence probe for visual and real-time detection of dichloromethane in water-miscible methanol to prepare a probe stock solution A with a concentration of 1 mmol·L–1; 2. Dilute the probe stock solution A obtained in step 1 with different solvents to obtain a probe solution B; 3. Add the probe solution A obtained in step 1 to the organic solvent to obtain a test solution C; 4. After the probe solution B and the test solution C are placed at room temperature for 30 seconds, measure the ultraviolet absorption spectra of each test solution. Under the conditions of an excitation wavelength of 330 nm and an excitation slit width of 5.0 nm, measure the fluorescence emission spectra of each test solution respectively. Whether the organic solvent is dichloromethane can be judged by the different ultraviolet absorption spectra and fluorescence emission spectra of the probe.