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A Fluorescent Probe for Detecting Amine Compound Gas

An amine compound and fluorescent probe technology, applied in the field of organic fluorescent sensors, can solve the problems of many synthesis steps, unfavorable development of portable solid fluorescent sensors, complex structure of fluorescent compounds, etc., and achieves the effects of rapid detection, simple structure and easy synthesis.

Active Publication Date: 2022-03-22
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing fluorescence sensors need to be dispersed in solutions or nanoparticles to emit fluorescence, and they need to be configured as a large-volume solution system for detection, which is not conducive to the development of portable solid-state fluorescence sensors.
Some organic fluorescent molecules that can be used to detect amine compounds have been reported in the literature (Chem.Commun., 2013, 49, 4848-4850), but the related fluorescent compounds have complex structures and many synthesis steps, which are not convenient to make portable A solid-state fluorescent sensor that can be used to detect amine compound gases

Method used

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  • A Fluorescent Probe for Detecting Amine Compound Gas
  • A Fluorescent Probe for Detecting Amine Compound Gas
  • A Fluorescent Probe for Detecting Amine Compound Gas

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] According to the synthetic route of the present invention, the compound of formula I with the following specific structure is synthesized:

[0037] Synthesis of ethyl 7-(benzo[d]oxazol-2-yloxy)-2-oxo-2H-benzyl-3-carboxylate

[0038]

[0039] In a 50ml round bottom flask, 7-hydroxy-2-oxo-2-H-methylene-3-carboxylic acid ethyl ester (167mg, 0.71mmol) and potassium carbonate (100mg, 0.71mmol) were dissolved in 25ml acetonitrile , the temperature was raised to reflux for 1 hour, then 2-chlorobenzoxazole (100 mg, 0.65 mmol) was added, and the reflux was continued for 5 hours. After the reaction was complete, it was filtered with suction, the filtrate was spin-dried, and an appropriate amount of methanol was added for recrystallization, and 179 mg of a light yellow solid was obtained by filtration, with a yield of 72%.

[0040] The structure of the product was characterized by H NMR and C NMR.

[0041] 1 H NMR (500MHz, DMSO-d 6 )δ8.85(s,1H),8.11(d,J=8.6Hz,1H),7.83(d,J=2...

Embodiment 2

[0043] Preparation of test strips.

[0044] Dissolve the compound 7-(benzo[d]oxazol-2-yloxy)-2-oxo-2H-benzyl-3-carboxylic acid ethyl ester in dichloromethane to prepare a concentration of 0.1mM A solution of this compound in dichloromethane. Take 20 μL of the solution and drop it on a strip of neutral filter paper, and let it dry naturally in a fume hood to prepare a detection test paper. The detection test paper is used for the detection test of the following examples.

Embodiment 3

[0046] The response of compound 7-(benzo[d]oxazol-2-yloxy)-2-oxo-2H-benzyl-3-carboxylic acid ethyl ester to different kinds of amine compounds.

[0047] Add 55 μL of 0.08M propylamine aqueous solution into a 5ml sealed bottle, let it stand for 1 hour until the concentration of propylamine gas reaches saturation, then place the detection test paper in the concentration of propylamine gas, take it out after 1 minute, and measure the fluorescence intensity with a fluorescence spectrophotometer , it was found that the fluorescence emission intensity at 445nm was significantly enhanced. Using a similar method, prepare cyclohexylamine, ethylenediamine, dimethylamine, diethylamine, triethylamine, pyridine, ammonia and hydrazine hydrate gases respectively, put the detection test paper into the corresponding gas, take it out after 1 minute, and pass Fluorescence spectrophotometer detects fluorescence intensity. The detection test paper also had fluorescent responses to these eight kin...

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Abstract

The invention discloses a fluorescent probe for detecting amine compound gas, and the probe is a coumarin derivative substituted by 2-hydroxybenzoxazole. The fluorescent probe described in the present invention is sensitive to amine compound gas, generates 7-hydroxycoumarin carboxylate through chemical reaction with amine compound gas, and emits bright blue fluorescence under the irradiation of ultraviolet light. The fluorescent probe of the present invention reacts with the amine compound gas under mild conditions, and can be made into a portable solid fluorescent sensor for rapid detection of the amine compound gas in the production environment and the living room environment.

Description

【Technical field】 [0001] The invention relates to a preparation method and application of 2-hydroxybenzoxazole-substituted coumarin compounds, especially the application in gas detection of amine compounds, and belongs to the field of organic fluorescent sensors. 【Background technique】 [0002] Amine compounds are widely used in the fields of chemical industry, medicine, food production and agriculture. At normal temperature, lower aliphatic amines are gases or are easily volatile and have an unpleasant odor. Aromatic amines are liquids or solids with a high boiling point. The smell is smaller than that of aliphatic amines, but they are relatively toxic. Inhalation of their vapors can cause poisoning. Amine compound gas is one of the sources of air pollution and one of the main sources of volatile organic substances in the living room. It is very harmful to human skin, respiratory system, nervous system, urinary system, hematopoietic system, etc., and can cause acute or del...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06G01N21/643C09K2211/1033C09K2211/1088
Inventor 陈绍晋胡志强孟媛媛房颖王鲲鹏杜春晖
Owner QINGDAO UNIV OF SCI & TECH