A fluorescent sensing material based on phenylthiazole and p-cyanobiphenol, its preparation method and application

A cyanobiphenol and phenylthiazole technology is applied in the field of chemical fluorescence sensing materials, which can solve the problems of inability to realize Fe3+ detection in biological cells, excessive introduction of organic solvents, complicated synthesis process, etc., and achieve simple and easy post-processing and purification. easy to control, the synthesis conditions are easy to control, and the synthesis conditions are mild

Active Publication Date: 2020-06-09
JIANGSU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently reported for the detection of Fe 3+ There are also many sensing materials, most of which are based on specific fluorescent groups such as rhodamine B and coumarin. Most of the molecular systems are too large and the synthesis process is complicated; and too many organic solvents are introduced during the detection process, which cannot be realized. Fe in biological cells 3+ detection, the application is limited

Method used

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  • A fluorescent sensing material based on phenylthiazole and p-cyanobiphenol, its preparation method and application
  • A fluorescent sensing material based on phenylthiazole and p-cyanobiphenol, its preparation method and application
  • A fluorescent sensing material based on phenylthiazole and p-cyanobiphenol, its preparation method and application

Examples

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Effect test

Embodiment 1

[0039] S1. Preparation of 2-amino-4-phenylthiazole: put 2.05g of acetophenone and 2.13g of thiourea into a round-bottomed flask, add 3.80g of iodine element, seal and react in an oil bath at 40°C for 24h, and react After the end, add hot water, stir and heat until it becomes a uniform solution system, filter, cool the filtrate to room temperature, then add ammonia water to adjust the pH to weak alkaline (pH=8), the product is precipitated and recrystallized in ethanol for purification.

[0040] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 0.5g of p-cyanobiphenol and 2.15g of hexamethylenetetramine were dissolved in 40mL of trifluoroacetic acid and placed in a round bottom flask at 100°C for 4 h under reflux. After the reaction, the reaction solution was cooled to room temperature, acidified by adding 1.0 M HCl (100 mL), and then extracted with dichloromethane. The collected organic layer was washed three times with water, dried over anhydrous magnesium sulfate, filter...

Embodiment 2

[0043] S1. Preparation of 2-amino-4-phenylthiazole: put 2.74g of acetophenone and 2.84g of thiourea into a round-bottomed flask, add 5.08g of iodine element, seal and react in an oil bath at 50°C for 27h, and react After the end, add hot water, stir and heat until it becomes a uniform solution system, filter, cool the filtrate to room temperature, then add ammonia water to adjust the pH to weak alkaline (pH=8), the product is precipitated and recrystallized in ethanol for purification.

[0044] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 1.0 g of p-cyanobiphenol and 5.30 g of hexamethylenetetramine were dissolved in 60 mL of trifluoroacetic acid and placed in a round bottom flask at 110°C for 6 h at reflux. After the reaction, the reaction solution was cooled to room temperature, acidified by adding 1.0 M HCl (100 mL), and then extracted with dichloromethane. The collected organic layer was washed three times with water, dried over anhydrous magnesium sulfate, filter...

Embodiment 3

[0047] S1. Preparation of 2-amino-4-phenylthiazole: put 3.42g of acetophenone and 3.55g of thiourea into a round-bottomed flask, add 6.35g of iodine element, seal and react in an oil bath at 60°C for 30h. After the reaction, add hot water, stir and heat until it becomes a uniform solution system, filter, cool the filtrate to room temperature, then add ammonia water to adjust the pH to weak alkaline (pH=8), the product is precipitated and recrystallized in ethanol for purification.

[0048] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 1.5g of p-cyanobiphenol and 6.45g of hexamethylenetetramine were dissolved in 80mL of trifluoroacetic acid and placed in a round bottom flask at 120°C for 8 h at reflux . After the reaction, the reaction solution was cooled to room temperature, acidified by adding 1.0 M HCl (100 mL), and then extracted with dichloromethane. The collected organic layer was washed three times with water, dried over anhydrous magnesium sulfate, filtered, an...

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Abstract

The invention relates to a fluorescence sensing material based on phenylthiazole and p-cyanodiphenol, as well as a preparation method and application of the fluorescence sensing material, and belongs to the technical field of a chemical fluorescence sensing material. The preparation method comprises the following steps: taking 2,6-dihydroxymethyl p-methylphenol and thiosemicarbazide as basic raw materials, performing reaction on the premise of taking acetophenone and thiourea as basic raw materials and taking an iodine elementary substance as a catalyst to prepare 2-amino-4-phenylthiazole; preparing 3-formyl-4-hydroxybenzyl cyanide by taking p-cyano-phenol as a basic raw material and under the existence of hexamethylenetetramine; performing nucleophilic reaction to combine the 2-amino-4-phenylthiazole and the 3-formyl-4-hydroxybenzyl cyanide to obtain the fluorescence sensing material. Due to the own conjugation structure, the fluorescence sensing material prepared by the method emits orange red fluorescence, has sensitive selective identification performance on heavy metal Fe<3+> and shows fluorescence quenching, the response time is short, the change of a fluorescence signal is visible to naked eyes under an ultraviolet lamp, and the interference of other common metal ions is small.

Description

technical field [0001] The invention relates to a fluorescent sensing material based on phenylthiazole and p-cyanobiphenol, a preparation method and application thereof, and belongs to the technical field of chemical fluorescent sensing materials. Background technique [0002] As the main pollutants in the environment, heavy metal ions have always been the focus of attention. Industrial production wastewater often contains a large amount of heavy metal ions, and improper treatment will cause serious harm to the environment. Since heavy metal pollutants cannot be degraded by microorganisms, once they enter the environment or ecosystem, they will persist and accumulate for a long time, and they are easily absorbed by organisms. Different forms of heavy metal ions will migrate and enrich through organisms. It acts on animals and plants, and finally enters the human body through the food chain to endanger health. [0003] As a heavy metal, iron is one of the essential trace el...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/42C09K11/06G01N21/64
CPCC07D277/42C09K11/06C09K2211/1007C09K2211/1037G01N21/6428G01N21/6486G01N2021/6432
Inventor 唐旭王赟李静韩娟李程刘仁杰王蕾倪良
Owner JIANGSU UNIV
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