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A polymer fluorescent sensor, preparation method and application based on porphyrin-based ratiometric detection of hypochlorite

A technology for detecting hypochlorous acid and fluorescence sensors, which is applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as the interference of biological autofluorescence, and achieve the effects of stable dispersion, simple preparation and high sensitivity

Active Publication Date: 2021-02-02
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some polymer-based hypochlorite ratiometric fluorescent sensors (CN201610689409.8, CN201610834650.5) have been developed, their fluorescence wavelength is in the visible light region, which cannot well avoid the interference of biological autofluorescence

Method used

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  • A polymer fluorescent sensor, preparation method and application based on porphyrin-based ratiometric detection of hypochlorite
  • A polymer fluorescent sensor, preparation method and application based on porphyrin-based ratiometric detection of hypochlorite
  • A polymer fluorescent sensor, preparation method and application based on porphyrin-based ratiometric detection of hypochlorite

Examples

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Effect test

Embodiment 1

[0043] A preparation of a polymer fluorescent sensor based on porphyrin-based ratiometric detection of hypochlorite, the specific steps are as follows:

[0044] (1) 5-(hydroxyphenyl)-10,15,20-phenylporphyrin (0.1 mmol), 2-methyl-2-(((propylthio)carbonylthio)thio)propane Acid (0.5 mmol), 4-dimethylaminopyridine (0.15 mmol), N,N'-diisopropylcarbodiimide (0.75 mmol) were dissolved in dichloromethane according to the molar ratio, and stirred at room temperature for 18 hours Finally, the reaction solution was washed with distilled water to remove N,N'-diisopropylcarbodiimide, and the product was purified by column after rotary evaporation and vacuum-dried to obtain compound 1.

[0045] (2) Dissolve compound 1 (0.02 mmol), styrene (3.5 mmol), and azobisisobutyronitrile (0.005 mmol) synthesized in step (1) in 1 mL of dimethylformamide (DMF), and vacuumize - Circulate three times with nitrogen gas and then rapidly raise the temperature to 90° C. for 6 h. After the reaction, precipita...

Embodiment 2

[0050] A preparation of a polymer fluorescent sensor based on porphyrin-based ratiometric detection of hypochlorite, the specific steps are as follows:

[0051] (1) 5-(hydroxyphenyl)-10,15,20-phenylporphyrin (0.1 mmol), 2-methyl-2-(((propylthio)carbonylthio)thio)propane Acid (0.3 mmol), 4-dimethylaminopyridine (0.05 mmol), N,N'-diisopropylcarbodiimide (0.5 mmol) were dissolved in dichloromethane according to the molar ratio, and stirred at room temperature for 12 hours Finally, the reaction solution was washed with distilled water to remove N,N'-diisopropylcarbodiimide, the product was purified by column after rotary evaporation, and dried in vacuum to obtain compound 1;

[0052] (2) Dissolve compound 1 (0.02 mmol), styrene (2 mmol), and azobisisobutyronitrile (0.004 mmol) synthesized in step (1) in 0.5 mL dimethylformamide (DMF), and vacuumize - Circulate three times with nitrogen gas and then rapidly raise the temperature to 80°C for 4 h. After the reaction, precipitate wit...

Embodiment 3

[0057] A preparation of a polymer fluorescent sensor based on porphyrin-based ratiometric detection of hypochlorite, the specific steps are as follows:

[0058] (1) 5-(hydroxyphenyl)-10,15,20-phenylporphyrin (0.1 mmol), 2-methyl-2-(((propylthio)carbonylthio)thio)propane acid (1 mmol), 4-dimethylaminopyridine (0.2 mmol), N,N'-diisopropylcarbodiimide 1.5 mmol) were dissolved in dichloromethane according to the molar ratio, and stirred at room temperature for 24 hours , wash the reaction solution with distilled water to remove N,N'-diisopropylcarbodiimide, then rotatively evaporate and pass the column to purify the product, and dry it in vacuum to obtain compound 1;

[0059] (2) Dissolve compound 1 (0.02 mmol), styrene (5 mmol), and azobisisobutyronitrile (0.006 mmol) synthesized in step (1) in 2 mL of dimethylformamide (DMF), and vacuumize - Circulate three times with nitrogen gas and then rapidly raise the temperature to 100°C for 8 h. After the reaction, precipitate with meth...

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Abstract

The invention discloses the preparation and application of a porphyrin-based polymer fluorescent sensor capable of ratiometric detection of hypochlorite. The fluorescent sensor is based on 5-(hydroxyphenyl)-10,15,20-phenyl porphyrin, 2‑Methyl‑2‑(((propylthio)carbonylthio)thio)propionic acid, a novel ratiometric fluorescent sensor prepared from styrene (St) and polyethylene glycol methyl ether (PEGMA) . The fluorescent sensor can realize the ratiometric detection of hypochlorite with high selectivity and high sensitivity in pure aqueous solution. Compared with the existing fluorescent detection technology, the fluorescent sensor obtained by the present invention has the advantages of high selectivity ratio to hypochlorite, low cytotoxicity, excellent water dispersibility, low input cost, simple synthesis route, etc., and is suitable for Amplified synthesis and practical production applications have great application prospects in technical fields such as analytical chemistry, life science, and environmental science.

Description

technical field [0001] The present invention relates to the preparation and application of a porphyrin-based fluorescent sensor capable of ratiometric detection of hypochlorite, specifically, the preparation and application of a polymer fluorescent sensor capable of ratiometric detection of hypochlorite, which belongs to the preparation and analysis of chemical materials detection field. Background technique [0002] As the most basic unit of life, cells have become an important part that human beings must pay close attention to in the study of life science. Among them, reactive oxygen species (ROS) is a very important species that widely exists in biological cells, and it plays a very important role in signal transduction, differentiation, migration and cellular immunity in biological cells. However, ROS all have the common characteristics of high activity, low content, and uneven distribution in organisms. How to explore their functions in organisms has become particularl...

Claims

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Application Information

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IPC IPC(8): C08G81/02G01N21/64C09K11/06
Inventor 曾荣今魏宏庆张培盛陈建张崇华
Owner HUNAN UNIV OF SCI & TECH
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