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AIE fluorescence probe molecule, and p-nitroaniline and fluoride ion detection methods thereof

A fluorescent probe and detection method technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problem of no discovery, achieve high sensitivity and selectivity, good application prospects, Strong photostability

Active Publication Date: 2018-08-24
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no fluoride ion fluorescent probe molecule based on 5-pyrene methylene rhodanine has been found so far.

Method used

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  • AIE fluorescence probe molecule, and p-nitroaniline and fluoride ion detection methods thereof
  • AIE fluorescence probe molecule, and p-nitroaniline and fluoride ion detection methods thereof
  • AIE fluorescence probe molecule, and p-nitroaniline and fluoride ion detection methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1, the preparation method of the synthetic (R=H) of fluorescent probe molecule 5-pyrene methylene rhodanine comprises the following steps:

[0035] (1) Add 0.046g (0.2mmol) pyrene formaldehyde, 0.0483g (0.3mmol) rhodanine and 3 drops of acetic acid into a 50mL three-necked flask, and dissolve with 8mL absolute ethanol;

[0036] (2) add 3 drops of pyridine to catalyze, and reflux at 80 degrees Celsius for 3 hours;

[0037] (3) After cooling, TLC detects that the reaction is complete, the solution is orange, and orange-red crystals are precipitated at the bottom after a long time;

[0038] (4) The solvent is removed by distillation under reduced pressure, with sherwood oil, methylene chloride and methanol of 3:7:0.5 as the mobile phase, separated by a silica gel column, and obtaining the target product 5-pyrene methylene rhodanine of orange-red powder, producing The rate is about 76.2%.

[0039] The structure confirmation data of the target product of the orange-red pow...

Embodiment 2

[0052] Replace R with an amino group or an aldehyde group, and the rest of the conditions are the same as in Example 1. AIE fluorescent probe molecules that can detect fluoride ions can be prepared, and the results are similar to those in Example 1.

Embodiment 3

[0054] 1, the preparation method of fluorescent probe molecule (R=CHO), the steps are as follows:

[0055] (1) Add 1.4728 g (4 mmol) of 5-pyrene methylene rhodanine (4 mmol) and 6.2411 g (85 mmol) of N,N-dimethylamide in Example 1 into a 100 mL three-necked flask, and place it in an ice bath at 0° C. Slowly add 3.2mL POCl dropwise within hours 3 , kept at 0°C for 1 hour in an ice bath, then raised the temperature to 90-100°C for about 24 hours under reflux;

[0056] (2) when it is cooled, the TLC detection reaction is complete, and the solution is black;

[0057] (3) Add 3 mL ice water for hydrolysis; cool to room temperature again, adjust the pH value to 5-6 with concentrated Na2CO3 solution, then extract with 3×30 mL toluene, and take the lower layer solution;

[0058] (4) wash with concentrated Na2CO3 solution and deionized water successively, remove the solvent by distillation under reduced pressure, use 3:2 petroleum ether and dichloromethane as the mobile phase, separa...

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Abstract

The invention relates to an AIE fluorescence probe molecule, and p-nitroaniline and fluoride ion detection methods thereof in order to solve the technical problems of poor identification ability and serious fluorescence quenching of fluorescence probes in the prior art. 5-pyrenylmethylenerhodanine is prepared from pyrenecarboxaldehyde and rhodanine by a simple synthesis technology with pyridine asa catalyst. The molecule has a good aggregation-induced luminescence effect, and is a highly-sensitive fluorescence probe molecule for detecting p-nitroaniline and fluoride ions.

Description

technical field [0001] The invention relates to the fields of aggregation-induced luminescent effect and fluorescent probes, in particular to an AIE fluorescent probe molecule and a detection method for p-nitroaniline and fluorine ions. Background technique [0002] The Aggregation-Induced Emission Effect (AIE) was first discovered by Academician Tang Benzhong's research group in 2001. Compared with traditional fluorescent chromophores, which will weaken or even not emit light at high concentrations, this type of polymer emits light in an aggregated state or a solid film This enhanced luminescence effect caused by aggregation is called "aggregation-induced luminescence effect". Based on the understanding and research of the AIE phenomenon, a series of AIE substances have been synthesized and made into efficient light-emitting devices and chemical biosensors. It is also true that the research on the mechanism of the AIE phenomenon has been carried out extensively and deeply....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/36C09K11/06G01N21/64
CPCC07D277/36C09K11/06C09K2211/1011C09K2211/1037G01N21/6428G01N2021/6432
Inventor 罗穗莲汪春朱益练昌周
Owner SOUTH CHINA NORMAL UNIVERSITY
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