Long wavelength type thiophenol fluorescent probe as well as preparation method and application thereof

A technology of fluorescent probes and thiophenols, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of poor selectivity, difficulty in combining long-wave emission, high selectivity and fast response, slow response, etc. problem, achieve rapid identification and detection, high selectivity and anti-interference ability, and avoid interference

Active Publication Date: 2017-06-20
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Comprehensive analysis of the current fluorescent probes for detecting PhSH, the shortcoming is that most of them are in the short wavelength region (λ em <600nm) for identification and detection, even if there are very few long-wave PhSH fluorescent probes, there are certain deficiencies such as poor selectivity or slow response, that is, it is difficult to have comprehensive performance such as long-wave emission, high selectivity and fast response.

Method used

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  • Long wavelength type thiophenol fluorescent probe as well as preparation method and application thereof
  • Long wavelength type thiophenol fluorescent probe as well as preparation method and application thereof
  • Long wavelength type thiophenol fluorescent probe as well as preparation method and application thereof

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Embodiment 1

[0032] A preparation method of a long-wave type thiophenol fluorescent probe, specifically comprising the following steps:

[0033] (1) Under ice cooling, add 172mg (0.2mmol) aminoporphyrin and 80mg (0.3mmol) 2,4-dinitrobenzenesulfonyl chloride to 15mL of anhydrous pyridine in turn, stir and dissolve, protect with nitrogen, and stir at room temperature The reaction was carried out for 6-8 hours, followed by TLC until the reaction was completed.

[0034] (2) Pour the above reaction solution into 150mL distilled water, filter, wash the filter cake with distilled water to obtain a purple solid; dissolve the purple solid in 20mL dichloromethane, wash with distilled water 3 times (20mL distilled water / time), and separate The organic layer was obtained, and the organic layer was dried over anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, purified by silica gel column chromatography, and dried in vacuum to obtain the target probe compound (TPP-DNBS).

Embodiment 2

[0036] A preparation method of a long-wave type thiophenol fluorescent probe, specifically comprising the following steps:

[0037] (1) Under ice cooling, add 0.3mmol aminoporphyrin and 0.4mmol 2,4-dinitrobenzenesulfonyl chloride to 20mL anhydrous pyridine successively, stir and dissolve, protect with nitrogen, stir at room temperature for 6~8h, TLC Follow up until the reaction is complete.

[0038] (2) Pour the above reaction solution into 200mL distilled water, filter, wash the filter cake with distilled water to obtain a purple solid; dissolve the purple solid in 25mL dichloromethane, wash twice with distilled water (20mL distilled water / time), and separate The organic layer was obtained, and the organic layer was dried over anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, purified by silica gel column chromatography, and dried in vacuum to obtain the target probe compound (TPP-DNBS).

Embodiment 3

[0040] A preparation method of a long-wave type thiophenol fluorescent probe, specifically comprising the following steps:

[0041] (1) Under ice cooling, add 0.3mmol aminoporphyrin and 0.5mmol 2,4-dinitrobenzenesulfonyl chloride to 30mL anhydrous pyridine in turn, stir and dissolve, protect with nitrogen, stir at room temperature for 6-8h, TLC Follow up until the reaction is complete.

[0042] (2) Pour the above reaction solution into 300mL distilled water, filter, wash the filter cake with distilled water to obtain a purple solid; dissolve the purple solid in 30mL dichloromethane, wash with distilled water 5 times (20mL distilled water / time), and separate The organic layer was obtained, and the organic layer was dried over anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, purified by silica gel column chromatography, and dried in vacuum to obtain the target probe compound (TPP-DNBS).

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Abstract

The invention discloses a long wavelength type thiophenol fluorescent probe as well as a preparation method and application thereof. According to the long wavelength type thiophenol fluorescent probe, amino porphyrin and 2,4-dinitrobenzenesulfonyl chloride are used as raw materials and proper reaction conditions are controlled to obtain a target probe compound. The fluorescent probe disclosed by the invention has a very long fluorescence emission wavelength (lambda-em is more than 650nm), rapid response and high anti-interference capability; high-selectivity and high-sensitivity fluorescent recognition and detection on trace thiophenol in a water environment and a biological sample can be realized; the long wavelength type thiophenol fluorescent probe has very good application prospect.

Description

technical field [0001] The invention relates to the technical field of preparation of fluorescent sensing materials and chemical analysis and detection, in particular to a long-wave type thiophenol fluorescent probe with the function of identifying and detecting thiophenol, its preparation method and application. Background technique [0002] PhSH (thiophenol) is a highly toxic environmental pollutant that widely exists in pharmaceutical, pesticide and chemical environments, such as in the synthesis of local anesthetics, organophosphorus pesticides and polymer resin vulcanizing agents. Low concentrations of PhSH have a strong stimulating effect on the skin, eyes, and mucous membranes, and can cause larynx and bronchospasm, muscle weakness, and chemical pneumonia. At high concentrations, it can paralyze the central nervous system or cause pulmonary edema and death. Therefore, the detection of PhSH in the environment or in vivo is of great significance. The detection of PhSH ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/6486
Inventor 曾荣今成奋民高倩陈国良杨赟山陈述龙云飞
Owner HUNAN UNIV OF SCI & TECH
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