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pH-responsive fluorescence sensing material based on rhodamine B and cyanobiphenol, preparation method and applications thereof

A cyanobiphenol and fluorescent sensing technology, which is applied in the field of biochemical fluorescent sensing materials, achieves the effects of easy control of conditions, mild conditions, and low preparation cost

Inactive Publication Date: 2018-02-16
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there have been a large number of reports on fluorescent materials that can be used to detect pH, but most of them can only measure the pH value in a small range of acid or alkali, and few materials can achieve a wide range from acidic to neutral to alkaline Determination of pH

Method used

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  • pH-responsive fluorescence sensing material based on rhodamine B and cyanobiphenol, preparation method and applications thereof
  • pH-responsive fluorescence sensing material based on rhodamine B and cyanobiphenol, preparation method and applications thereof
  • pH-responsive fluorescence sensing material based on rhodamine B and cyanobiphenol, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] S1. Synthesis of rhodamine B hydrazide: Dissolve 1 g (2 mmol) rhodamine B in 20 mL of methanol, add 2 mL of 85% hydrazine hydrate dropwise while stirring, and place in a 60°C oil bath after the addition is complete Heat and stir to reflux for 8h. After the reaction is completed, cool to room temperature and remove the solvent under reduced pressure to obtain a crude product, which is purified by recrystallization in methanol.

[0035] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 0.39g (2mmol) of p-cyanobiphenol and 1.41g (10mmol) of urotropine were completely dissolved in 30 mL of trifluoroacetic acid and placed in a round bottom In the flask, heat and stir in an oil bath at 100°C to reflux for 4 hours. After the reaction is complete, cool the system to room temperature, add 100 mL of 1.0 M dilute HCl to the system for acidification, then extract the product with dichloromethane, collect the dichloromethane phase and wash it three times with distilled water, an...

Embodiment 2

[0038] S1. Synthesis of Rhodamine B Hydrazide: Dissolve 1.5g (3mmol) Rhodamine B completely in 30mL of methanol, add 3.7 mL of 85% hydrazine hydrate dropwise while stirring, and place in a 65°C oil bath after the addition is complete Heating in medium temperature and stirring to reflux for 10 h, after the reaction was completed, cooled to room temperature, and removed the solvent under reduced pressure to obtain a crude product, which was purified by recrystallization in methanol.

[0039] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 0.78g (4mmol) of p-cyanobiphenol and 2.82g (20mmol) of urotropine were completely dissolved in 50 mL of trifluoroacetic acid and placed in a round bottom In the flask, heat, stir and reflux in an oil bath at 110°C for 6h. After the reaction is complete, cool the system to room temperature, add 100 mL of 1.0 M dilute HCl to the system for acidification, then extract the product with dichloromethane, collect the dichloromethane phase and wa...

Embodiment 3

[0042] S1. Synthesis of Rhodamine B Hydrazide: Dissolve 2g (4mmol) Rhodamine B in 40mL of methanol, add 5 mL of 85% hydrazine hydrate dropwise while stirring, and place in a 70°C oil bath after the addition is complete Heat and stir to reflux for 12 hours. After the reaction is complete, cool to room temperature and remove the solvent under reduced pressure to obtain a crude product, which is purified by recrystallization in methanol.

[0043] S2. Preparation of 3-formyl-4-hydroxybiphenylcyanide: 1.17 g (6 mmol) p-cyanobiphenol and 4.23 g (30 mmol) urotropine were completely dissolved in 70 mL trifluoroacetic acid and placed in a round bottom In the flask, heat, stir and reflux in an oil bath at 120°C for 8 hours. After the reaction is complete, cool the system to room temperature, add 100 mL of 1.0 M dilute HCl to the system for acidification, then extract the product with dichloromethane, collect the dichloromethane phase and wash it three times with distilled water, and dry...

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Abstract

The present invention relates to a pH-responsive fluorescence sensing material based on rhodamine B and cyanobiphenol, a preparation method and applications thereof, and belongs to the technical fieldof biochemical fluorescent sensing materials. According to the present invention, two pH-sensitive optical groups such as rhodamine B and cyanobiphenol are used base raw materials, wherein rhodamineB and hydrazine hydrate are subjected to a reaction to prepare rhodamine B hydrazide, and then the rhodamine B hydrazide and aldehyde-modified cyanobiphenol are combined through a Schiff base reactionto prepare the fluorescence sensing material; the method has advantages of mild preparation conditions and low raw material cost; the prepared material has good chemical stability, and has unique response properties to different pH values, wherein the responses can be presented through visible fluorescence and appearance color; and the prepared pH-responsive fluorescence sensing material can be used for the determination of the pH value in water and biological cells.

Description

technical field [0001] The present invention relates to a preparation method and application of a fluorescent chemical sensing material, in particular to a pH-responsive fluorescent sensing material based on rhodamine B and cyanobiphenol and its preparation method and application, belonging to biochemical fluorescent sensing field of materials technology. Background technique [0002] Usually the conduct and completion of some chemical reactions and various physiological processes in organisms are closely related to pH. The intracellular pH value plays an important role in important biological processes such as ion transport, phagocytosis, cell proliferation or apoptosis, and homeostasis. The pH environment of different tissues in biological cells is also different. The pH value of lysosome and endosome is acidic, in the range of 4.5–6.8; the pH in cytoplasm and active mitochondria is alkaline, in the range of 6.8–8 Inside. When the pH of a certain part of the cell is abn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/80
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/6428G01N21/643G01N21/80G01N2021/6439
Inventor 唐旭王赟韩娟李春梅刘仁杰李程王蕾倪良
Owner JIANGSU UNIV
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