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A kind of is used for detecting pH fluorescent probe molecule and preparation method thereof

A fluorescent probe and molecule technology, applied in the field of fluorescent probe molecules and their preparation, achieves the effects of good specificity, excellent application prospects and fast detection speed

Active Publication Date: 2022-03-25
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there is an urgent need to develop a fluorescent probe molecule that has the above advantages and is simple to prepare and easy to operate to meet the needs of efficient detection of pH, so as to solve the current shortcomings of on-site and rapid detection of pH.

Method used

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  • A kind of is used for detecting pH fluorescent probe molecule and preparation method thereof
  • A kind of is used for detecting pH fluorescent probe molecule and preparation method thereof
  • A kind of is used for detecting pH fluorescent probe molecule and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of fluorescent probe molecule 2-(3-amino-4-carboxyphenyl)benzothiazole:

[0038] a. 4mmol of 2-amino-terephthalic acid, 0.725g, 4mmol of 2-aminobenzenethiol, 0.5g, 4.8mmol of triphenyl phosphite, 1.489g and 4.8mmol of tetrabutylammonium bromide, 1.163g Add it to a 50mL three-neck round bottom flask, stir evenly, slowly heat to a temperature of 120°C, reflux for 12 hours, and stop the reaction;

[0039] b. After the reaction is cooled to room temperature, add 120 mL of a mixed solvent of methanol and deionized water at a volume ratio of 1:1, filter out the precipitate, and dry to obtain a crude product;

[0040] c. Purify the crude product obtained in step b through forward silica gel chromatography, eluting with petroleum ether and ethyl acetate at a volume ratio of 1:1, and then drying the eluted product to obtain Fluorescent probe molecule 2-(3-amino-4-carboxyphenyl)benzothiazole in yellow solid to detect pH;

[0041] figure 1 It is the NMR data of the pr...

Embodiment 2

[0044] Synthesis of fluorescent probe molecule 2-(2-amino-3-carboxyphenyl)benzothiazole:

[0045] a. 4mmol of 2-amino-isophthalic acid, 0.725g, 4mmol of 2-aminobenzenethiol, 0.5g, 4.8mmol of triphenyl phosphite, 1.489g and 4.8mmol of tetrabutylammonium bromide, 1.163g Add to a 50mL three-neck round bottom flask, stir evenly, slowly heat to a temperature of 100°C, reflux for 6 hours, and stop the reaction;

[0046] b. After the reaction is cooled to room temperature, add 120 mL of a mixed solvent of methanol and deionized water at a volume ratio of 1:1, filter out the precipitate, and dry to obtain a crude product;

[0047] c. Purify the crude product obtained in step b through forward silica gel chromatography, eluting with petroleum ether and ethyl acetate at a volume ratio of 1:1, and then drying the eluted product to obtain Fluorescent probe molecule 2-(2-amino-3-carboxyphenyl)benzothiazole in yellow solid for pH detection.

Embodiment 3

[0049] Synthesis of fluorescent probe molecule 2-(4-amino-3-carboxyphenyl)benzothiazole:

[0050] a. 4mmol of 4-amino-isophthalic acid, 0.725g, 4mmol of 2-aminobenzenethiol, 0.5g, 4.8mmol of triphenyl phosphite, 1.489g and 4.8mmol of tetrabutylammonium bromide, 1.163g Add to a 50mL three-neck round bottom flask, stir evenly, slowly heat to a temperature of 100°C, reflux for 6 hours, and stop the reaction;

[0051] b. After the reaction is cooled to room temperature, add 120 mL of a mixed solvent of methanol and deionized water at a volume ratio of 1:1, filter out the precipitate, and dry to obtain a crude product;

[0052] c. Purify the crude product obtained in step b through forward silica gel chromatography, eluting with petroleum ether and ethyl acetate at a volume ratio of 1:1, and then drying the eluted product to obtain Fluorescent probe molecule 2-(4-amino-3-carboxyphenyl)benzothiazole in yellow solid for pH detection.

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Abstract

The invention discloses a fluorescent probe molecule for detecting pH and a preparation method thereof. The compound N-aminophthalic acid, 2-aminobenzenethiol, triphenyl phosphite and tetrabutylammonium bromide are mixed together. Heat the reaction under air atmosphere, after the reaction is completely cooled to room temperature, add a mixed solvent of methanol or acetone and deionized water to obtain the crude product; after the crude product is separated and purified by silica gel chromatography, a light yellow solid fluorescent probe for detecting pH is obtained Molecule 2‑(N‑amino‑N+1 carboxyphenyl)benzothiazole. The pH value is detected by the change of fluorescence spectral signal. Due to the specific chemical reaction between the acid-base component and the probe molecule in the pH to form a reaction product with a specific structure, the specificity and selectivity of the detection are greatly improved, and the secondary pollution of the acid-base is avoided. The preparation process of the present invention is simple. It has low cost, excellent selectivity and sensitivity, can be used for rapid detection of pH value, and has broad application prospects.

Description

technical field [0001] The invention relates to a fluorescent probe molecule used for pH detection and a preparation method thereof, which belongs to the field of organic chemistry and analysis and detection, and realizes the detection of pH value through the change of fluorescence spectrum and spectrum color. Background technique [0002] Acidity or alkalinity (pH) is a very important key parameter that regulates many chemical / physiological processes in various fields such as life sciences, crop and food production, medical diagnosis and decontamination of the environment (J.Agric.Food Chem.2019, 67, 1222–1229). Furthermore, in biological systems, pH plays a crucial role in many physiological processes, regulation and homeostasis are prerequisites for the survival of living cells; such as cell proliferation and apoptosis, ion transport, enzyme activity and protein degradation (J. Am. Chem. Soc. 2013, 135, 4926-4929). Highly sensitive detection of pH is essential for medic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/643C09K2211/1007C09K2211/1037
Inventor 窦新存马志伟李继广胡晓云
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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