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1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole ratiometric fluorescence or ratiometric ultraviolet absorption probe agent and preparation and application thereof

A quinoline oxymethyl, ratiometric fluorescence technology, applied in fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve problems such as aluminum ion toxicity, and achieve novel compound structures, high yields, and simple synthesis methods. Effect

Active Publication Date: 2014-07-30
广西平果润民脱贫发展有限公司
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Problems solved by technology

But in recent years, more and more evidence proves that aluminum ions have great toxicity to the human central nervous system

Method used

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  • 1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole ratiometric fluorescence or ratiometric ultraviolet absorption probe agent and preparation and application thereof
  • 1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole ratiometric fluorescence or ratiometric ultraviolet absorption probe agent and preparation and application thereof
  • 1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole ratiometric fluorescence or ratiometric ultraviolet absorption probe agent and preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment one: compound a That is, the synthesis of 1-(7-coumarinethoxy)-4-(2-methyl-8-quinolineoxymethyl)-1,2,3-triazole:

[0058] In a 100ml three-necked flask under nitrogen protection, add 1.00g (6.29mmol) of 8-hydroxyquinaldine, 1.30g (9.44mmol) of potassium carbonate and 50ml of acetone, reflux for 0.5h, cool, and then add 3-bromopropyne 1.05 g Gray intermediate: 2-methyl-8-(prop-2-ynyloxy)quinoline, yield 85.0%.

[0059] In a 100ml three-necked flask under nitrogen protection, add 2.34g (10.15mmol) of 7-(2-azidoethoxy)-coumarin, 1.00g (5.76mmol) of the above intermediate and cuprous iodide (catalytic amount), reacted at room temperature for 10h, finished, filtered, the filtrate was concentrated to remove the solvent, and purified by column chromatography, the eluent was: ethyl acetate / petroleum ether (1 / 1, v / v) to obtain 1.73g of the white target product a : 1-(7-coumarinethoxy)-4-(2-methyl-8-quinolineoxymethyl)-1,2,3-triazole, yield 70.0%. m.p.141~143℃; 1 ...

Embodiment 2

[0061] The preparation method of various reagents in various analytical methods of the present invention is:

[0062] (1) compound a Compound solution preparation method: weigh 4.3 mg of compound a , dissolved in ethanol to prepare a 100mL solution with a concentration of 100μmol L -1 ;

[0063] (2)Al 3+ Standard solution: weigh analytically pure Al(NO 3 ) 3 9H 2 O 75.0mg, dissolved in twice distilled water, and prepared into 100mL solution, Al 3+ The concentration is 2.00×10 -3 mol L -1 ; Dilute step by step with double distilled water to a suitable concentration as required;

[0064] (3) Preparation of other coexisting ionic solutions: Take analytically pure nitrates or hydrochlorides of various metals, dissolve them in double distilled water, and prepare them at a concentration of 2.00×10 -3 mol L -1 double distilled aqueous solution.

[0065] The used ultraviolet-visible spectrophotometer model of the present invention is UV-1800, and Shimadzu Corporation p...

Embodiment 3

[0068] Add compound to 10.0 mL volumetric flask a ethanol stock solution (1.00 x 10 -4 mol L -1 , 1mL), metal ion Al 3+ (2.00×10 -3 mol L -1, 1 mL), dilute to the mark with ethanol / water (2 / 3, v / v) solution, shake well, transfer to a 1cm quartz cuvette for fluorescence spectrum and ultraviolet absorption spectrum measurement.

[0069] Set the fluorescence excitation wavelength to 318nm, add about 3ml of compound into a 1cm cuvette a (Concentration is 1.00×10 -5 mol L -1 ) in ethanol / water (2 / 3, v / v) solution for fluorescence spectrum test, compound a There is fluorescence emission at a wavelength of 390 nm. Join Al 3+ (Concentration is 2.00×10 -4 mol L -1 ), the compound a The fluorescence intensity at 390nm of the solution was significantly reduced (quenching rate was 90.46%), and an emission peak appeared at 480nm (fluorescence intensity was 145). The wavelengths are 390nm and 480nm respectively to form a ratio fluorescence, and there is an iso-emission poi...

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Abstract

The invention provides a 1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole ratiometric fluorescence or ratiometric ultraviolet absorption probe agent and preparation and application thereof, and belongs to the technical fields of organic synthesis and analytic chemistry. The preparation method is characterized in that an intermediate, namely, 2-methyl-8-(propyn-2-yl alkoxy) quinoline, reacts with 7-(2-azidoethoxy)-coumarin to obtain a compound a of which triazolyl is connected with two fluorophores, namely, coumarin and quinoline, wherein the compound is 1-(7-ethoxycoumarin)-4-(2-methyl-8-methoxyquinoline)-1, 2, 3-triazole. The preparation method has the advantages that the reaction raw materials are easy to obtain, the synthesis method is simple, and the compound can be obtained by three-step reaction; the compound a generates ratiometric fluorescence at 480nm and 390nm in alcohol / aqueous solution, and trace Al<3+> can be measured accordingly; ratiometric ultraviolet absorption is produced at 253nm and 243nm, and trace Al<3+> can be measured accordingly. The probe agent is the probe agent being high in sensitivity, high in accuracy and high in selectivity and used for detecting Al<3+> ions through ratiometric fluorescence and ratiometric ultraviolet absorption. The structure formula of the compound a is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, specifically 1-(7-coumarin ethoxy)-4-(2-methyl-8-quinoline oxymethyl)-1,2,3- Triazole ratio fluorescence or ratio ultraviolet absorption probe reagent and its preparation and application. Background technique [0002] With the continuous improvement of people's requirements on the living environment and the deepening of life science understanding, it is an important topic to detect harmful or life-related ions with high sensitivity. As a highly selective and sensitive analytical detection technology, fluorescent probes have been rapidly developed in the detection of metal ions and acid ions and the recognition of certain neutral molecules (such as sugars and amino acids). Fluorescent probes are a class of organic molecules that can recognize ions and molecules and effectively express the measured ions or molecules through optical signals. Fluorescent reagents that recog...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D405/14G01N21/64G01N21/33
Inventor 赵远会牟兰曾晞李俊
Owner 广西平果润民脱贫发展有限公司
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