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Visible and reversible ratiometric fluorescent probe as well as preparation method and application thereof

A ratiometric fluorescent probe and reaction technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of reducing pollution, saving resources, and high sensitivity

Inactive Publication Date: 2015-11-11
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a kind of ratiometric fluorescent chemical probe that visually and reversibly detects sulfur dioxide gas and its derivatives in the air. The technical problem to be solved is to utilize the red fluorescent cyanine group and the blue fluorescent benzothiazole Groups designed as ratiometric fluorescent probes for visual and reversible detection of gaseous pollutants sulfur dioxide and its derivatives

Method used

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  • Visible and reversible ratiometric fluorescent probe as well as preparation method and application thereof
  • Visible and reversible ratiometric fluorescent probe as well as preparation method and application thereof
  • Visible and reversible ratiometric fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of ratiometric fluorescent probe 5-1 (R is propanesulfonic acid), the structural formula is as follows

[0046]

[0047] Take 5mL of salicylaldehyde and 2.35g of paraformaldehyde in a 250mL round-bottomed flask containing 20mL of concentrated hydrochloric acid. After the mixture is evenly mixed, start adding 1.5mL of POCl dropwise. 3 , added within 1 hour, the mixture was reacted at room temperature for 18 hours, and the precipitate was filtered out and washed with 3% NaHCO 3 After washing with ultrapure water three times respectively, put it into a vacuum drying oven to dry, then recrystallize with petroleum ether to obtain product 1, mass spectrometry ESI-MS: m / z (%): 169.59 (M - -1).

[0048] Add 12.5mmol of product 1 and 16.2mmol of cyclohexamethylenetetramine to 13mL of 50% acetic acid solution, heat to 120°C, reflux the reaction solution, add 6mL of concentrated hydrochloric acid after 1 hour, the solution turns yellow, continue After stirring for...

Embodiment 2

[0056] Preparation of ratiometric fluorescent probe 5-2 (R is 3-bromopropionic acid), the structural formula is as follows

[0057]

[0058] Take 5mL of salicylaldehyde and 2.35g of paraformaldehyde in a 250mL round-bottomed flask containing 20mL of concentrated hydrochloric acid. After the mixture is evenly mixed, start adding 1.5mL of POCl dropwise. 3 , added within 1 hour, the mixture was reacted at room temperature for 18 hours, and the precipitate was filtered out and washed with 3% NaHCO 3 and ultrapure water for three times, put it in a vacuum oven for drying, and recrystallize with petroleum ether to obtain product 1.

[0059] Add 12.5mmol of product 1 and 16.2mmol of cyclohexamethylenetetramine to 13mL of 50% acetic acid solution, heat to 120°C, reflux the reaction solution, add 6mL of concentrated hydrochloric acid after 1 hour, the solution turns yellow, continue After stirring for 5 minutes in an ice-water bath, the crude product precipitated out, and the light...

Embodiment 3

[0066] Preparation of ratiometric fluorescent probe 5-3 (R is bromoacetic acid), the structural formula is as follows

[0067]

[0068] Take 5mL of salicylaldehyde and 2.35g of paraformaldehyde in a 250mL round-bottomed flask containing 20mL of concentrated hydrochloric acid. After the mixture is evenly mixed, start adding 1.5mL of POCl dropwise. 3 , added within 1 hour, the mixture was reacted at room temperature for 18 hours, and the precipitate was filtered out and washed with 3% NaHCO 3 and ultrapure water for three times, put it in a vacuum oven for drying, and recrystallize with petroleum ether to obtain the product 1.

[0069] Add 12.5mmol of product 1 and 16.2mmol of cyclohexamethylenetetramine to 13mL of 50% acetic acid solution, heat to 120°C, reflux the reaction solution, add 6mL of concentrated hydrochloric acid after 1 hour, the solution turns yellow, continue After stirring for 5 minutes in an ice-water bath, the crude product precipitated out, and the light ...

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Abstract

The invention discloses a visible and reversible fluorescent probe which comprises a cyanine fluorescent group and a benzothiazole group, and the general formula of the probe is shown in the description. The preparation method of the reversible fluorescent probe comprises the following steps: (1) dropwise adding phosphorus oxychloride into salicylaldehyde and paraformaldehyde for reaction, so as to obtain a product 1; (2) enabling the product 1 and hexamethylene-tetramine to react, so as to obtain a product 2; (3) enabling the product 2 and 2-aminobenzenethiol to react at the room temperature, so as to obtain a product 3; (4) enabling the product 3 and a compound 4 to react, so as to obtain the visible and reversible fluorescent probe. According to the ratiometric fluorescent probe provided by the invention, obvious color variation can be found out under natural light or an ultra-violet lamp, and the qualitative detection of sulfur dioxide gas can be implemented under natural light or a hand-held ultra-violet lamp, so that the operation is simple, high convenience and quickness are achieved, and the effect is remarkable; the fluorescent probe can effectively prevent interference from other impurities in samples, and is excellent in selectivity; in addition, the cumbersome pre-processing process of samples is avoided, so that the detection efficiency is high.

Description

technical field [0001] The invention relates to a functionalized visible and reversible fluorescent probe and its preparation method and application, in particular to a visible and reversible fluorescent detection probe for trace gas pollutants and its preparation method. Background technique [0002] In the past ten years, my country's economy has undergone earth-shaking changes, and science and technology have also made great progress, but it has also caused a series of environmental pollution problems. Among them, air pollution is one of the most prominent problems at present. Among the six standard pollutants stipulated by EPA (Environment Protection Agency), sulfur dioxide is the largest pollutant therein. Sulfur dioxide generally enters the human body through the respiratory tract. Because it is easily soluble in water, many of them are blocked in the upper respiratory tract, and then form its derivatives such as sulfurous acid and sulfate, which further irritate the r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D417/10G01N21/64
Inventor 王素华张亚娇孙明泰
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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