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A fluorescent molecular probe for detecting formaldehyde and its preparation method, and a preparation method of its fluorescent test paper

A fluorescent molecular probe, formaldehyde technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problem that requires tens of minutes or even hours, and trace formaldehyde cannot be quantitatively detected. , unable to adapt to the complex and changeable environment and other problems, to achieve the effect of short response time, conducive to large-scale production, and reduce fluorescence loss

Active Publication Date: 2022-04-01
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent 201610981466.3 "A Class of Fluorescent Probes for Detecting Formaldehyde and Its Preparation and Application" discloses a kind of fluorescent probe that has no fluorescence in aqueous solution, but can react specifically and quickly with formaldehyde to generate a product with strong fluorescence, which detects formaldehyde The speed is only 1min, but its sensitivity to low concentration of formaldehyde is not high
Patent application No. 201710358356.6 "Preparation method and application of a fluorescent probe for detecting formaldehyde" reports a fluorescent probe for 2-aza-Cope rearrangement reaction, but its detection limit is at the mM level
Most of these fluorescent probes that have been reported so far have some limitations 1. The detection limit is limited and the response to formaldehyde is not sensitive enough
Mainly can only detect formaldehyde at the micromolar level, but cannot achieve quantitative detection of trace formaldehyde
2. The response speed is not fast enough, most probes need tens of minutes or even hours to complete the response after adding formaldehyde
3. The probes have poor solubility, and most of them can only be used in organic solvents, which limits their application in the environmental and biological fields
4. There are few types of probes and a single detection method, which cannot adapt to complex and changeable environments

Method used

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  • A fluorescent molecular probe for detecting formaldehyde and its preparation method, and a preparation method of its fluorescent test paper
  • A fluorescent molecular probe for detecting formaldehyde and its preparation method, and a preparation method of its fluorescent test paper
  • A fluorescent molecular probe for detecting formaldehyde and its preparation method, and a preparation method of its fluorescent test paper

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Embodiment 1

[0036] R in the fluorescent probe structural formula prepared in this embodiment 1 = H, R 2 =H.

[0037] The synthesis technical route of the present embodiment is as follows:

[0038]

[0039] Synthesis of compound 2

[0040] First, weigh isatoic anhydride (1.0g, 6.13mmol) into a 350mL round bottom flask, add 15mL of glacial acetic acid, stir and mix at room temperature, then weigh 2-aminothiophenol (0.85mL, 7.97mmol) and add to the reaction system, and then the reaction system was moved to a water bath environment, the temperature of the water bath was set at 90°C, and the reaction time was 2h. During the reaction process, the reaction system gradually changed from a turbid state to a clear state, and the color gradually changed from taupe to orange-yellow; TLC monitored the reaction process, and the dark spots of raw materials gradually decreased, producing blue fluorescent spots with less polarity, and by-products less. After the reaction was finished, the reaction...

Embodiment 2

[0051] Preparation of probe master solution

[0052] Accurately weigh 4.3 mg of the fluorescent molecular probe prepared in Example 1, place it in a 50 mL brown volumetric flask, add DMSO:H at room temperature 2 O=1:1 to make it fully dissolved, and constant volume to the mark, the obtained solution is 1mM probe mother solution.

[0053] Preparation of formaldehyde mother liquor:

[0054] Use a pipette gun to accurately measure 76uL and 760uL of 37% formaldehyde aqueous solution; transfer them to 10mL volumetric flasks, add deionized water at room temperature to fully dissolve, and dilute to the mark to obtain a solution of 100mM and 1000mM formaldehyde stock solution.

[0055] Fluorescence Response of Fluorescent Probes to Formaldehyde

[0056] Take 20 μL of the probe mother solution and 0, 6, 10, 20, 30, 40, 60, 100, 200, 240, 300, 360, 400 μL of the formaldehyde mother solution and place them in the test system, fully dissolve, and the total volume of the test system fo...

Embodiment 3

[0059] The solution prepared in Example 2 was used as a fluorescent probe, and the selectivity of the probe to formaldehyde was evaluated. The excitation wavelength of the nanoprobe was 365 nm. We have selected a variety of common small molecule aldehyde-containing compounds: 1. Benzaldehyde, 2. Acetaldehyde, 3. Propionaldehyde, 4. Methyl formate, 5. Ethyl formate, 6. Glyoxal, 7. Acetone, 8. Acetic acid, 9. Furfural, and 10. Formaldehyde were formulated into aqueous solutions and added to the probe solution at a concentration of 20 μM, and the probe concentration was 10 μM, where DMF: H 2 O=1:1 (v / v), pH value is 7.0, measure its fluorescence emission spectrum and record the intensity of fluorescence emission at 525nm. The result is as image 3 As shown, it is found that the fluorescent probe only has obvious fluorescence enhancement at 525nm for formaldehyde, and the fluorescence changes for other tested small molecules are weak, indicating that it has excellent selectivity ...

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Abstract

The invention discloses a fluorescent molecular probe for detecting formaldehyde and its preparation method, as well as a preparation method of the fluorescent test paper. The highly sensitive fluorescent detection of formaldehyde in acidic and neutral aqueous solutions provides favorable conditions for the detection of the fluorescent probe in complex environments. The fluorescent probe of the present invention has a fluorescent parent nucleus with an ESIPT effect as a fluorophore, which can reduce fluorescence loss, self-absorption, and biological background fluorescence to effectively improve detection sensitivity. The preparation method of the fluorescent probe molecule and the detection test paper of the present invention is simple and low in cost, and is favorable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and chemical analysis, and in particular relates to a fluorescent molecular probe for detecting formaldehyde and a preparation method thereof, and a preparation method of fluorescent test paper thereof. Background technique [0002] Formaldehyde is an important organic raw material, mainly used in plastic industry, synthetic fiber, leather industry, medicine, dyestuff, etc. At the same time, the harm of formaldehyde to the environment and human body cannot be ignored. Formaldehyde is a protoplasm poisonous substance that can be combined with protein. Its effects on human health are mainly manifested in abnormal sense of smell, abnormal pulmonary function, abnormal liver function, and abnormal immune function. Long-term exposure to low-dose formaldehyde can cause chronic respiratory diseases, reduced physical fitness of newborns, chromosomal abnormalities, and even nasopharyngeal cancer....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/10C09K11/06G01N21/64
CPCC07D417/10C09K11/06G01N21/6428G01N21/643G01N2021/6432C09K2211/1029C09K2211/1037C09K2211/1007
Inventor 曾文彬毕桉耀刘翊高瑭冯斌吴佳欣
Owner CENT SOUTH UNIV