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Novel hydrazine fluorescence probe for coumarin derivative

A technology of coumarin derivatives and fluorescent probes, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problems of complex synthesis process, low sensitivity, slow response, etc., and achieve operational steps Simple, low environmental requirements, good selective effect

Active Publication Date: 2019-07-09
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on fluorescent probes for hydrazine detection, and most of them have some limitations, such as limited low pH conditions, complicated synthesis process, slow reaction or low sensitivity, etc.

Method used

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  • Novel hydrazine fluorescence probe for coumarin derivative
  • Novel hydrazine fluorescence probe for coumarin derivative
  • Novel hydrazine fluorescence probe for coumarin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of 7-N,N-Diethylamino-coumarin-3-carbaldehyde

[0026] Diethylamino salicylaldehyde (0.965 g, 5 mol), diethyl malonate (1.6 g, 1.53 mL), piperidine (0.5 mL) were added to 15 ml of absolute ethanol and refluxed for 18 h (120°C ), distilled under reduced pressure (oil), 20 ml of concentrated hydrochloric acid and 20 ml of glacial acetic acid were added to the solution, and stirred at 115°C for 19 h. Cool the solution to room temperature, pour it into 100 mL of ice water, then add NaOH dropwise to adjust the pH to 5 (discoloration of the solution) and precipitate immediately, stir for 1 h, filter with suction, wash with water, and dry to obtain a matcha-colored solid. Add 6.5 mL redistilled N,N-dimethylformamide dropwise to 6.5 mL POCl 3 in N 2 Stirred under protective conditions for 30 min, the solution gradually turned yellow. Dissolve the matcha-colored solid in 30 mL of N,N-dimethylformamide, and add it dropwise to the yellow solution to generate a dark ...

Embodiment 2

[0030] Preparation of novel hydrazine fluorescent probes for coumarin derivatives

[0031] (1) Take 0.15 mL of 2-hydroxyacetophenone and 0.245 g of 7-N,N-diethylamino-coumarin-3-carbaldehyde, pour it into a 50 mL flask, add 0.7 mL of pyrrolidine as catalyst, and then added 18 mL of absolute ethanol as a solvent, and stirred at room temperature for 12 h. Filter and wash 3 times with absolute ethanol, and dry to obtain pure intermediate a, which is a red solid.

[0032] The synthetic route is as follows:

[0033] .

[0034] (2) Add 0.0363 g of a and 0.0715 g of levulinic acid into a 100 mL volumetric flask, add 18 mL of anhydrous dichloromethane, and use EDC as a condensation agent and DMAP as a catalyst, add 0.024 g respectively, 0.001 g, reacted at room temperature for 8 h, and then purified it by silica gel chromatography to obtain an orange solid, which was the final product CCL. 1 HNMR (CDCl 3 , 400MHz), δ (ppm): 1.24 (t, J = 7.1Hz, 6H), 2.20 (s, 3H), 2.87 (s,4H), ...

Embodiment 3

[0038] Exploration of solute chromogenic phenomenon of novel hydrazine fluorescent probe

[0039] In n-hexane, toluene, tetrahydrofuran, acetone, acetonitrile, dimethyl sulfoxide, methanol, and water, add the fluorescent probe at an initial concentration of 1 mM, so that the concentration of the fluorescent probe in the solution is 10 μM. Make its fluorescence spectrum change curve in different polar solvents. Such as figure 1 The results show that with the increase of solvent polarity, the fluorescence peak has obvious red shift, showing excellent solute color development.

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Abstract

The invention discloses a novel fluorescence probe for detecting hydrazine as well as a preparation method and application of the novel fluorescence probe. The probe has a molecular formula: C27H29NO5and has a structure as shown in the specification. The probe has very strong fluorescence and shows a very strong solubilization color rendering phenomenon. The fluorescence probe shows luminous yellow fluorescence in a mixed solution of DMSO and HEPES in the ratio of 4:1, but is turned into blue fluorescence after interacting with hydrazine. The fluorescence probe disclosed by the invention hasexcellent selectivity, relatively high sensitivity and obvious phenomenon when being used for detecting hydrazine, and the effect of identifying hydrazine by using the probe is still not affected whenthe pH value in a detection environment is 3-12. The preparation method of the novel fluorescence probe is simple, and the prepared product is high in yield.

Description

technical field [0001] The invention relates to a novel fluorescent probe for hydrazine detection, in particular to a method for preparing a hydrazine fluorescent probe of coumarin derivatives and its application to hydrazine recognition in an aqueous system. Background technique [0002] As an important class of heterocyclic compounds, coumarin derivatives have good physical and biological properties. In recent years, photophysical properties such as high fluorescence quantum yield, large Stokes shift, excellent photostability, and low toxicity of coumarin derivatives have been increasingly studied. [0003] Hydrazine (N 2 h 4 ) is a fuel widely used in missile and rocket propulsion systems and a reactant in fuel cells. And because of its high alkalinity and reducing properties, hydrazine has been widely used as an industrial chemical. However, hydrazine is highly toxic to humans and animals, and its concentration is too high, it will cause respiratory tract infection, ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/16G01N21/64
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1088G01N21/643G01N21/6447
Inventor 曹笃霞邢苗苗朱奕霖
Owner UNIV OF JINAN
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