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V-type coumarin fluorescent probe for hydrazine hydrate detection and preparation method thereof

A fluorescent probe, coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited number of fluorescent probes, influence of interfering ions, complex probe synthesis, etc., to prevent interference , the effect of simple synthesis and low cost

Active Publication Date: 2019-11-22
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the number of reports on fluorescent probes for the detection of hydrazine hydrate is limited, and many probes are complex to synthesize and are easily affected by interfering ions.

Method used

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  • V-type coumarin fluorescent probe for hydrazine hydrate detection and preparation method thereof
  • V-type coumarin fluorescent probe for hydrazine hydrate detection and preparation method thereof
  • V-type coumarin fluorescent probe for hydrazine hydrate detection and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] (1) Dissolve 13 mmol of diethyl malonate and 5 mmol of salicylaldehyde in 20 mL of ethanol, add dropwise two drops of glacial acetic acid and 0.1 mL of piperidine, and stir under reflux for 6 h at room temperature; add ice water after the reaction is complete A precipitate was precipitated, filtered and washed with ice water to obtain ethyl coumarin-3-carboxylate as a white solid;

[0029] (2) Mix 5 mmol of ethyl coumarin-3-carboxylate and 2.5 mmol of resorcinol, add 0.02 g of DMAP, and 2 Heated to 140°C under protection, reacted for 3 h, added ethanol and sonicated for 10 min, filtered and rinsed with ethanol to obtain V-type coumarin in the form of orange-yellow solid;

[0030] (3) Mix and dissolve 5 mmol V-type coumarin and 7 mmol 4-fluorobutyric acid in 20 mL of dichloromethane, add 0.02 g DMAP and 0.2 g DCC, stir at room temperature for 4 h, and distill off the solvent under reduced pressure The crude probe was obtained and purified by column chromatography with d...

Embodiment 2

[0032] (1) Dissolve 13 mmol of diethyl malonate and 5 mmol of salicylaldehyde in 20 mL of ethanol, add dropwise two drops of glacial acetic acid and 0.1 mL of piperidine, and stir at room temperature for 8 h under reflux; after the reaction is complete, add ice water A precipitate was precipitated, filtered and washed with ice water to obtain ethyl coumarin-3-carboxylate as a white solid;

[0033] (2) Mix 5 mmol of ethyl coumarin-3-carboxylate and 2.5 mmol of resorcinol, add 0.02 g of DMAP, and 2 Heated to 140°C under protection, reacted for 4 h, added ethanol and sonicated for 15 min, filtered and rinsed with ethanol to obtain V-type coumarin in the form of orange-yellow solid;

[0034] (3) Mix and dissolve 5 mmol V-type coumarin and 7 mmol 4-chlorobutyric acid in 20 mL of dichloromethane, add 0.02 g DMAP and 0.2 g DCC, stir at room temperature for 6 h, and distill off the solvent under reduced pressure The crude probe was obtained and purified by column chromatography with ...

Embodiment 3

[0036] (1) Dissolve 13 mmol of diethyl malonate and 5 mmol of salicylaldehyde in 20 mL of ethanol, add dropwise two drops of glacial acetic acid and 0.1 mL of piperidine, and stir under reflux for 6 h at room temperature; add ice water after the reaction is complete A precipitate was precipitated, filtered and washed with ice water to obtain ethyl coumarin-3-carboxylate as a white solid;

[0037] (2) Mix 5 mmol of ethyl coumarin-3-carboxylate and 2.5 mmol of resorcinol, add 0.1 g of AlCl 3 , at N 2 Heated to 140°C under protection, reacted for 3 h, added ethanol and sonicated for 10 min, filtered and rinsed with ethanol to obtain V-type coumarin in the form of orange-yellow solid;

[0038] (3) Mix and dissolve 5 mmol V-type coumarin and 7 mmol 4-chlorobutyric acid in 20 mL of dichloromethane, add 0.02 g DMAP and 0.2 g DCC, stir at room temperature for 5 h, and distill off the solvent under reduced pressure The crude probe was obtained and purified by column chromatography wi...

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Abstract

The invention belongs to the technical field of fluorescent probe preparation, and particularly relates to a V-type coumarin fluorescent probe for hydrazine hydrate detection and a preparation methodthereof. Under the excitation of ultraviolet light, the probe compound does not emit fluorescence itself, but when the probe compound reacts with hydrazine hydrate, a substitution cyclization reactionof a halogenated butyrate ester chain can occur so that the probe emits yellow fluorescence, and detection of the hydrazine hydrate is realized. Tests prove that the fluorescent probe has very strongselectivity and very high sensitivity to the hydrazine hydrate, can respond to the hydrazine hydrate in a complex environment, is an excellent Turbn-on type fluorescent probe, and has a very good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe preparation, and in particular relates to a V-type coumarin fluorescent probe and a preparation method thereof. Background technique [0002] Hydrazine hydrate is a colorless oily liquid with an ammonia-like odor, and its molecular formula is N 2 h 4 ·H 2 O, due to the existence of hydrogen bonds, it has a relatively high melting point and boiling point, and is easily soluble in water and other polar solvents. In both solid and liquid states, hydrazine hydrate is monohydrate. Hydrazine hydrate has a wide range of uses and is often used as pharmaceutical intermediates, foaming agents, fuel cells, insecticides, etc. Due to its high combustion enthalpy, hydrazine hydrate is also often used in aerospace fuel and missile propulsion systems. However, hydrazine hydrate is also a highly toxic substance, which is easily ingested by the human body through the mouth, skin and respiratory system,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C09K11/06G01N21/64
CPCC07D493/04C09K11/06C09K2211/1088G01N21/643
Inventor 侯琳熙姜行宗卢振曾晓扬张永乐
Owner FUZHOU UNIV