A kind of preparation method and application of bis-Schiff base-based fluorescent sensing material

A fluorescent sensing and bi-Schiff base technology, applied in the field of chemical fluorescent sensing materials, can solve problems such as changes in cell membrane permeability and cell membrane dysfunction, and achieve the effects of shortening the reaction time, enhancing water solubility, and stabilizing the structure

Active Publication Date: 2020-06-26
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, mercury can combine with the sulfhydryl group on the cell membrane, causing a change in the permeability of the cell membrane, resulting in a serious obstacle to the function of the cell membrane.

Method used

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  • A kind of preparation method and application of bis-Schiff base-based fluorescent sensing material
  • A kind of preparation method and application of bis-Schiff base-based fluorescent sensing material
  • A kind of preparation method and application of bis-Schiff base-based fluorescent sensing material

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Effect test

Embodiment 1

[0037] Step 1. Preparation of 2,6-diacetaldehyde-4-methylphenol: Put 1g of 2,6-dimethylol-p-methylphenol in a round-bottomed flask, dissolve it in 20 mL of acetonitrile, 65°C oil After stirring in the bath for 30 minutes, add 6 g of active manganese dioxide, stir and reflux at 110 ° C for 65 hours, cool to room temperature after the reaction, filter to remove the oxidant manganese dioxide, collect the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain a crude product. Purified by recrystallization in ethanol to obtain a pale yellow solid.

[0038] Step 2. Preparation of fluorescent sensing materials based on bis-Schiff bases: 0.164g of 2,6-diacetaldehyde-4-methylphenol and 0.182g of thiosemicarbazide were placed in a round bottom flask, and 20mL of anhydrous Dissolve it in ethanol, and add 2 drops of glacial acetic acid as a catalyst. Stir and reflux in an oil bath at 65°C for 5 h, cool to room temperature after the reaction, and remove th...

Embodiment 2

[0040] Step 1. Preparation of 2,6-diacetaldehyde-4-methylphenol: Put 3g of 2,6-dimethylol-p-methylphenol in a round-bottomed flask, dissolve it in 40 mL of acetonitrile, 65°C oil After stirring in the bath for 30 minutes, add 18 g of active manganese dioxide, stir and reflux at 130 ° C for 80 hours, cool to room temperature after the reaction, filter to remove the oxidant manganese dioxide, collect the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain a crude product. Purified by recrystallization in ethanol to obtain a pale yellow solid.

[0041] Step 2. Preparation of fluorescent sensing materials based on bis-Schiff bases: 0.492g of 2,6-diacetaldehyde-4-methylphenol and 0.546g of thiosemicarbazide were placed in a round-bottomed flask, and 40mL of anhydrous Dissolve it in ethanol, and add 2 drops of glacial acetic acid as a catalyst. Stir and reflux in an oil bath at 75°C for 7 hours, cool to room temperature after the reaction, and re...

Embodiment 3

[0043] Step 1. Preparation of 2,6-diacetaldehyde-4-methylphenol: Put 2g of 2,6-dimethylol-p-methylphenol in a round-bottomed flask, dissolve it in 30 mL of acetonitrile, 65°C oil After stirring in the bath for 30 minutes, add 12 g of active manganese dioxide, stir and reflux at 120 ° C for 72 hours, cool to room temperature after the reaction, filter to remove the oxidant manganese dioxide, collect the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain a crude product. Purified by recrystallization in ethanol to obtain a pale yellow solid.

[0044] Step 2. Preparation of fluorescent sensing materials based on bis-Schiff bases: 0.328g of 2,6-diacetaldehyde-4-methylphenol and 0.364g of thiosemicarbazide were placed in a round-bottomed flask, and 30mL of anhydrous Dissolve it in ethanol, and add 2 drops of glacial acetic acid as a catalyst. Stir and reflux in an oil bath at 70°C for 6 hours, cool to room temperature after the reaction is comp...

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Abstract

The invention relates to a preparation method and application of a bis-schiff base based fluorescent sensing material and belongs to the technical field of chemical fluorescent sensing materials. 2,6-dihydroxymethyl phenol p-methyl phenol and thiosemicarbazide are adopted as basic raw materials, active manganese dioxide firstly serves as an oxidizing agent to oxidize the 2,6-dihydroxymethyl phenol p-methyl phenol into aldehyde, then glacial acetic acid is adopted as a catalyst to prepare the fluorescent sensing material through nucleophilic reaction and the thiosemicarbazide. The prepared material is based on symmetrical bis-schiff base, is stable in structure, and the water-soluble thiosemicarbazide is introduced to make the water solubility of the sensing material greatly enhanced. The prepared fluorescent sensing material has dual response, respectively has the sensitive selective recognition properties on Hg<2+> and Zn<2+>, shows different fluorescence emissions, is short in response time, is macroscopic under change of fluorescence signals of an ultraviolet lamp, and other common metal ion interferences are small.

Description

technical field [0001] The invention relates to a preparation method and application of a fluorescent chemical sensing material, in particular to a preparation method and application of a bis-Schiff base-based fluorescent sensing material, 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. With the progress of industry and the development of social economy, people have carried out extensive mining, smelting, processing and commercial manufacturing of heavy metals in nature, causing serious heavy metal ion pollution to the surrounding environment, seriously affecting ecology and human health. and security. Production enterprises such as coal mines, metal sulfide mines, iron ore and metallurgy often produce a large amount of wastewater containing metal ions, and improper treatment will cause serious harm to the environme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/29C07C47/565C07C337/08C09K11/06G01N21/64
CPCC07C45/298C07C337/08C09K11/06C09K2211/1007G01N21/6428G01N21/643G01N21/6486C07C47/565
Inventor 唐旭韩娟王赟倪良王蕾李程刘仁杰
Owner JIANGSU UNIV
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