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Ratio fluorescent probe as well as preparation method and application thereof

A fluorescent probe, ratio-based technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited probe practical application, insignificant color change, long probe response time, etc. The effect of promoting application, high sensitivity and accuracy, and low cost

Active Publication Date: 2019-06-21
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, most of these fluorescent probes output a single fluorescent signal, which will affect the accuracy of detection, while the other part of the probes have shortcomings such as too long response time, insufficient sensitivity, too high detection limit, and no obvious color change. The above-mentioned technical problems have severely limited the practical application of these probes.

Method used

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  • Ratio fluorescent probe as well as preparation method and application thereof
  • Ratio fluorescent probe as well as preparation method and application thereof
  • Ratio fluorescent probe as well as preparation method and application thereof

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preparation example Construction

[0043] The present invention also provides a method for preparing a ratiometric fluorescent probe, comprising the following steps:

[0044] a) Mix triphenylbromoethylene and 3-formyl-4-hydroxyphenylboronic acid pinacol ester in the presence of toluene, potassium carbonate solution and tetrabutylammonium bromide, and then add a catalyst for the first reaction , compound A is obtained after the first separation and purification; the catalyst is tetrakis (triphenylphosphine) palladium (0);

[0045] The compound A has a structure shown in formula (II):

[0046]

[0047] b) The compound A obtained in step a) and 2-benzimidazole acetonitrile are reacted for the second time in the presence of ethanol and piperidine, and the ratiometric fluorescent probe is obtained after the second separation and purification;

[0048] The ratiometric fluorescent probe has a structure shown in formula (I):

[0049]

[0050] The present invention first mixes triphenylbromoethylene and 3-formyl...

Embodiment 1

[0079] (1) Dissolve 670mg of triphenylbromoethylene in 20mL of toluene, add 4mL of potassium carbonate solution and 50mg of tetrabutylammonium bromide under stirring, then add 500mg of 3-formyl-4-hydroxyphenylboronic acid pinacol ester, stirred at room temperature for 20 min, and finally added 10 mg of catalytic amount of tetrakis(triphenylphosphine) palladium (0), heated to 90°C for 24 h under nitrogen protection, added ethyl acetate after cooling, washed with water 3 times, and organically The phase was dried over anhydrous sodium sulfate and concentrated, and the reaction crude product was purified by column chromatography to obtain 306 mg of light yellow compound A (yield 41%).

[0080] (2) Dissolve 188mg of compound A and 78.5mg of 2-benzimidazole acetonitrile in 7.5mL of ethanol, add 40μL of piperidine, heat to 80°C under nitrogen protection for 1h, filter after cooling to room temperature, and wash with ethanol for 3 times After vacuum drying, 190.5 mg of milky white pr...

Embodiment 2

[0083] (1) Dissolve 670 mg of triphenylbromoethylene in 25 mL of toluene, add 6 mL of potassium carbonate solution and 70 mg of tetrabutylammonium bromide under stirring, and then add 600 mg of 3-formyl-4-hydroxyphenylboronic acid pinacol ester, stirred at room temperature for 30 min, and finally added 15 mg of catalytic amount of tetrakis(triphenylphosphine) palladium (0), heated to 95 °C for 22 h under nitrogen protection, added ethyl acetate after cooling, washed with water for 3 times, and organically The phase was dried and concentrated over anhydrous sodium sulfate, and the crude reaction product was purified by column chromatography to obtain 331 mg of pale yellow compound A (yield 44%).

[0084] (2) Dissolve 188mg of Compound A and 86.5mg of 2-benzimidazole acetonitrile in 9mL of ethanol, add 50μL of piperidine, heat to 82°C under nitrogen protection and reflux for 1.2h, cool to room temperature, filter, and wash with ethanol for 3 times After vacuum drying, 198.5 mg o...

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Abstract

The invention provides a ratio fluorescent probe as well as a preparation method and application thereof. The preparation method comprises the following steps: (a) mixing triphenyl bromoethylene and 3-formyl-4-hydroxyphenylboronic acid pinacol ester in the existence of toluene, a potassium carbonate solution and tetrabutylammonium bromide, adding a catalyst to perform a primary reaction, and performing primary separation and purification to obtain a compound A, wherein the catalyst is palladium (0) tetraphenylphosphine, and the compound A has the structure shown in formula II; (b) performing secondary reaction on the compound A which is obtained in the step (a) and 2-benzimidazolyl in the existence of ethanol and piperidine, and performing secondary separation and purification to obtain the ratio fluorescent probe, wherein the ratio fluorescent probe has the structure which is shown in formula (I). Compared with the prior art, the ratio fluorescent probe provided by the invention can realize the change of double fluorescence signals in the existence of low-concentration phosgene, is high in sensitivity and accuracy, and has high selectivity on the phosgene, quick response and low detection limit.

Description

technical field [0001] The invention relates to the technical field of environmental analysis and detection, and more specifically relates to a ratio-type fluorescent probe and its preparation method and application. Background technique [0002] Phosgene (COCl 2 ), also known as carbonyl chloride, is a highly toxic gas with strong chemical reactivity. As early as World War II, phosgene was used as a chemical weapon in warfare. At the same time, phosgene has high chemical reactivity and is a very important chemical raw material, which plays a huge role in industrial production. However, phosgene is an extremely dangerous colorless gas, and it is not easy to detect its existence, and the symptoms of poisoning will not appear immediately after the low concentration of phosgene is inhaled. Edema, suffocation, and even death. The leakage of phosgene poses a great threat to the environment and human life safety, so convenient, rapid and real-time visual monitoring of phosgene ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/64
Inventor 胡清华王宏青黄秋香刘波谭芳容谭艳红
Owner NANHUA UNIV
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