An enhanced fluorescent probe, its preparation method and its application in the detection of formaldehyde

A fluorescent probe, enhanced technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as detection selectivity and poor sensitivity

Active Publication Date: 2020-09-22
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, only a small number of fluorescent probes for the detection of formaldehyde have been reported, and most of them have the problems of poor detection selectivity and sensitivity

Method used

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  • An enhanced fluorescent probe, its preparation method and its application in the detection of formaldehyde
  • An enhanced fluorescent probe, its preparation method and its application in the detection of formaldehyde
  • An enhanced fluorescent probe, its preparation method and its application in the detection of formaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] 330.1 mg of compound 1 (1.1 mM) was dissolved in 18 ml of THF under ice-bath conditions, and 831.1 mg of p-nitrobenzaldehyde (5.5 mM) and 345.6 mg of sodium cyanoborohydride (5.5 mM) and 660 mg of acetic acid ( 11.0mM), remove the ice bath, stir at room temperature, and protect with nitrogen. Reaction more than 10h. After the reaction, the reaction solution was removed by a vacuum rotary evaporator to remove the solvent to obtain a crude product, and a silica gel (200-300 mesh) chromatography column was carried out with ethyl acetate and petroleum ether at a volume ratio of 12:1 as eluents. Purification afforded 180.1 mg of white solid (37.4% yield).

Embodiment 2

[0021]

[0022] 100.4mg of compound 1 (0.34mM) was dissolved in 8ml of THF under ice-bath conditions, and 256.9mg of p-nitrobenzaldehyde (1.70mM) and 128.2mg of sodium cyanoborohydride (2.04mM) and 360.3mg of Acetic acid (6.0mM), remove the ice bath, stir at room temperature, nitrogen protection. Reaction more than 10h. After the reaction, the reaction solution was removed by a vacuum rotary evaporator to remove the solvent to obtain a crude product, and a silica gel (200-300 mesh) chromatography column was carried out with ethyl acetate and petroleum ether at a volume ratio of 12:1 as eluents. Purification afforded 29.5 mg of white solid (20.1% yield).

Embodiment 3

[0024]

[0025] 175.5mg of compound 1 (0.59mM) was dissolved in 14ml of THF under ice-bath conditions, and 624.5mg of p-nitrobenzaldehyde (4.13mM) and 259.5mg of sodium cyanoborohydride (4.13mM) and 474.4mg of Acetic acid (7.9mM), remove the ice bath, stir at room temperature, nitrogen protection. Reaction more than 10h. After the reaction, the reaction solution was removed by a vacuum rotary evaporator to remove the solvent to obtain a crude product, and a silica gel (200-300 mesh) chromatography column was carried out with ethyl acetate and petroleum ether at a volume ratio of 12:1 as eluents. Purification afforded 74.1 mg of white solid (29.1% yield).

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PUM

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Abstract

The invention discloses an enhanced type fluorescent probe. The formaldehyde fluorescent probe disclosed by the invention has a following structural formula which is shown in the description. The invention further provides a preparation method of the fluorescent probe. The fluorescent probe disclosed by the invention has no fluorescence in a buffer solution, but can generate specific reaction withformaldehyde to generate a product with strong fluorescence; thus, specific response to the formaldehyde is achieved. The probe has good stability and can be stored and used for a long time. The probe has strong antijamming capability and very good selectivity to the formaldehyde.

Description

technical field [0001] The invention relates to a preparation method of a switch-type formaldehyde fluorescent probe and its application in detecting the formaldehyde content in the environment, belonging to the field of environmental analytical chemistry and biological detection. Background technique [0002] Formaldehyde, with the molecular formula HCHO, is the simplest aldehyde. It is a colorless gas with a special irritating odor, which has irritating effects on human eyes and nose, and has sensitization, teratogenic and carcinogenic toxicity to human body. Formaldehyde in indoor air, atmospheric environment and food pollution can lead to poisoning, causing dizziness, headache or nausea, vomiting, severe memory loss and even death. Under normal circumstances, there is a complete metabolic mechanism in the body, which can generally degrade formaldehyde into CO through enzymatic reactions. 2 , formic acid and water, if excessive formaldehyde accumulates in the body, it w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06C09K2211/1007C09K2211/1037G01N21/643
Inventor 郑开波李梦周洋曾繁伟晏佳莹张诺诺
Owner CHINA THREE GORGES UNIV
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