A fluorescent probe for recognizing chloride ions and its preparation method and application

A fluorescent probe, chloride ion technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limiting anion species and fluorescence response sensitivity, achieve strong resistance to other molecular interference, post-processing process Simple, selective effect

Active Publication Date: 2022-05-10
SHIJIAZHUANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The working mechanism of traditional anionic fluorescent probes is to use strong hydrogen bonds between anions and fluorescent probes, and complete detection by photoinduced charge transfer or changing the conformation of fluorophores. This method has certain limitations. The anion species detected and the sensitivity of the fluorescence response

Method used

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  • A fluorescent probe for recognizing chloride ions and its preparation method and application
  • A fluorescent probe for recognizing chloride ions and its preparation method and application
  • A fluorescent probe for recognizing chloride ions and its preparation method and application

Examples

Experimental program
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Effect test

preparation example Construction

[0028] The preparation method of the above-mentioned fluorescent probe for recognizing chloride ions comprises the following steps:

[0029] Step 1, 6-methoxyquinoline was dissolved in C 2 h 5 OH to obtain the first solution, 3-bromopropylamine hydrobromide dissolved in CH 3 The second solution was obtained in CN; the above two solutions were mixed and heated to a reaction temperature of 75-85°C, and the crude product obtained after the reaction was purified and separated to obtain the compound represented by formula (3);

[0030] .

[0031] The reaction formula is expressed as:

[0032]

[0033] Step 2, dissolving the compound represented by formula (3) obtained in step 1 and benzenesulfonyl chloride in dichloroethane, and separating and purifying after completion of the stirring reaction to obtain the target probe compound represented by formula (4).

[0034] The reaction formula is expressed as:

[0035]

[0036] Relatively specifically, the above-mentioned met...

Embodiment 1

[0045] Step 1, the synthesis of the compound shown in formula (3):

[0046] Dissolve 6-methoxyquinoline (10.0 mmol, 1.59 g) in 10 mL C 2 h 5 In OH, 3-bromopropylamine hydrobromide (10 mmol, 2.19 g) was dissolved in 2 mL CH 3 In CN, the above two solutions were mixed, heated to a reaction temperature of 80°C, and the reaction time was 6 hours, a white precipitate was formed, the crude product was centrifuged at 8000 rpm for 5 min, the precipitate was collected, and washed with C 2 h 5 Wash with OH until there is no 6-methoxyquinoline in the supernatant, and vacuum-dry the white precipitate to obtain the pure compound of formula (3), with a yield of 84%.

[0047] Step 2, the synthesis of the target probe compound:

[0048] Dissolve 1.00 mmol of the compound of formula (3) (0.203 g) and 1.00 mmol of benzenesulfonyl chloride (0.176 g) in 10 mL of dichloroethane, stir and react for 4 h, filter the precipitate in the system and recrystallize with ethanol to obtain pure Product,...

Embodiment 2

[0050] The difference from Example 1 is only that in step 1, the reaction temperature is 75° C., and the reaction time is 8 hours.

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Abstract

The invention relates to a chloride ion fluorescent probe with fast response time and high selectivity, a preparation method and application thereof. The molecular formula of the fluorescent probe molecule is: C 19 h 21 N 2 o 3 S + , the structural formula is shown in formula 4. Dissolve 6‑methoxyquinoline in C 2 h 5 OH to obtain the first solution, 3‑bromopropylamine hydrobromide dissolved in CH 3 The second solution was obtained in CN; the above two solutions were mixed and heated to a reaction temperature of 75-85°C, the crude product obtained after the reaction was purified and separated, and the compound and benzenesulfonyl chloride obtained were dissolved in dichloroethane, and the reaction was completed with stirring After separation and purification, the target probe compound was obtained. The invention realizes the selective rapid detection of the chloride ion molecular probe, has good selectivity and strong anti-interference ability of other molecules. In addition, the color change of the solution can be observed with the naked eye, and the fluorescence color change can also be observed under the ultraviolet light. Formula 4.

Description

technical field [0001] The invention relates to the technical field of organic small molecule fluorescent probes, in particular to a fluorescent molecular probe for recognizing chloride ions and its preparation method and application. Background technique [0002] Chloride ion is the most common anion in water and wastewater. Excessively high concentration of chloride ion will cause bitter and salty drinking water, soil salinization, pipeline corrosion, difficult plant growth, and endanger human health. Therefore, chloride ion must be controlled emission concentration. Determining the content of chloride ions in the body and the natural environment has very important scientific significance. [0003] Fluorescent probe technology has become a commonly used chemical analysis method because of its advantages of high sensitivity and low detection limit. For the detection of chloride ions, the conventional methods are chemical titration and other electrochemical methods, which ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/20C09K11/06G01N21/64
CPCC07D215/20C09K11/06G01N21/643G01N21/6428G01N21/6447G01N21/6486C09K2211/1029C09K2211/1007G01N2021/6432
Inventor 张玲刘凯娜徐薇王羽菲
Owner SHIJIAZHUANG UNIVERSITY
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