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A kind of multifunctional fluorescent probe with esipt and aie properties and its preparation method and application

A fluorescent probe, multi-functional technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of complex synthesis process, unfavorable environmental protection, poor solubility, etc., and achieve simple synthesis method and good sensitivity , the effect of simplifying the identification process

Active Publication Date: 2022-03-18
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many of the currently reported fluorescent probes that can be used for relay recognition of copper ions and pyrophosphate need to be used in mixed solvents containing more organic solvents, which is not conducive to environmental protection.
Few fluorescent probes that can relay copper ions and pyrophosphate in aqueous solution have the disadvantage of complex synthesis process
[0003] Using the excited-state intramolecular proton transfer (ESIPT) property, it is possible to obtain longer fluorescence emission from small molecule fluorophores, but when this type of probe is used in a mixed solvent with high water content, it is often due to poor solubility. However, it is constrained by the aggregation-induced quenching (ACQ) effect
[0004] At present, it has ESIPT and AIE properties, and can relay recognition of copper ions and pyrophosphate fluorescent probes in solvents with high water content, which has not been reported in the literature.

Method used

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  • A kind of multifunctional fluorescent probe with esipt and aie properties and its preparation method and application
  • A kind of multifunctional fluorescent probe with esipt and aie properties and its preparation method and application
  • A kind of multifunctional fluorescent probe with esipt and aie properties and its preparation method and application

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Experimental program
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Embodiment

[0036] (1) The reaction formula of the synthetic relay type multifunctional fluorescent probe:

[0037]

[0038] (2) Concrete steps for synthesizing relay-type multifunctional fluorescent probes:

[0039] Weigh 0.185g of 2-pyridinecarboxylic acid and dissolve it in 15mL of dry dichloromethane, add 0.682g of benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and stir for 30 minutes, then added 0.226g 2-(2′-aminophenyl)benzothiazole and 0.181g triethylamine, and stirred at 25°C for 12h. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was separated by column chromatography with the eluent of ethyl acetate and petroleum ether at a volume ratio of 1:10 to obtain a relay-type multifunctional fluorescent probe N-(2-(2 '-Benzothiazolyl)phenyl)pyridinamide, yield 90%. Melting point: 165.5-166.1°C.

[0040] The results of NMR analysis are as Figure 1-3 Shown: 1 H NMR (400MHz, DMSO-d 6 )δ14.15(s,1H),8.98...

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Abstract

A multifunctional fluorescent probe with ESIPT and AIE properties and its preparation method and application, the preparation method of the fluorescent probe is: dissolving 2-picolinic acid in dry dichloromethane, adding benzotriazole- N,N,N',N'-Tetramethyluronium hexafluorophosphate was stirred for 30 minutes, then 2-(2'-aminophenyl)benzothiazole and triethylamine were added, and stirred overnight at room temperature; After the end, the solvent was distilled off under reduced pressure, and the residue was separated by column chromatography to obtain the fluorescent probe N-(2-(2'-benzothiazolyl)phenyl)pyridinamide. The fluorescent probe of the present invention has a simple synthesis method, an easy product separation and purification process, has the property of "ESIPT+AIE", and can be used for monitoring, analysis and tracing of copper ions and pyrophosphate in water environment systems, and for the determination of target ions Has good sensitivity.

Description

technical field [0001] The invention relates to the field of functional materials, in particular to a multifunctional fluorescent probe with ESIPT and AIE properties and its preparation method and application. Background technique [0002] Fluorescent recognition of copper ions and pyrophosphate (PPi) is of great significance in life sciences and environmental monitoring, and has attracted much attention in recent years. Relay identification enables the identification of two ions to be performed continuously under the same test conditions, which has the obvious advantage of simple operation. Many of the currently reported fluorescent probes that can be used for relay recognition of copper ions and pyrophosphate need to be used in mixed solvents containing more organic solvents, which is not conducive to environmental protection. Few fluorescent probes that can recognize copper ions and pyrophosphate in aqueous solution have the disadvantage of complicated synthesis process....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C09K11/06G01N21/64
CPCC09K11/06C07D417/12G01N21/643C09K2211/1007C09K2211/1029C09K2211/1037G01N2021/6432
Inventor 汤立军夏俊影钟克利
Owner BOHAI UNIV
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