Quinaldine derivative b fluorescent and colorimetric reagent as well as preparation method and application thereof

A derivative, quinaldine technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve high yield, low detection limit, and simple synthesis method

Inactive Publication Date: 2014-03-19
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Using organic molecules with typical structures as a platform to design and prepare various fluorescent probe molecules with high sensitivity, good selectivity, and superior optical properties, the relevant research is very interesting in terms of the novelty of the molecular structure and the feasibility of the synthetic process route. challenge

Method used

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  • Quinaldine derivative b fluorescent and colorimetric reagent as well as preparation method and application thereof
  • Quinaldine derivative b fluorescent and colorimetric reagent as well as preparation method and application thereof
  • Quinaldine derivative b fluorescent and colorimetric reagent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Synthesis of intermediate a, namely (E)-2-(2,4-diacetoxyphenyl)vinyl-8-acetoxyquinoline:

[0066] In a 100ml three-necked flask under nitrogen protection, add 1.00g (6.29mmol) of 8-hydroxyquinaldine, 20ml of acetic anhydride and 1.74g (12.58mmol) of 2,4-dihydroxybenzaldehyde, heat to reflux for 5h, and concentrate to remove the solvent Acetic anhydride, purified by column chromatography, eluent: chloroform / ethyl acetate ( V:V =3:1) to obtain 1.78g of white target product a with a yield of 70.0%. m.p.131~133℃; 1 H NMR (400MHz, CDCl 3 )δ: 2.31(s, 3H, -COCH 3 ), 2.40(s, 3H, -COCH 3 ), 2.53(s, 3H, -COCH 3 ), 6.99(d, J=2.4Hz, 1H, ArH), 7.06-7.09(m, 1H, ArH), 7.30(s, 1H, ArH), 7.42-7.50(m, 2H, ArH), 7.58(d , J=8.4Hz, 1H, ArH), 7.67-7.78(m, 3H, ArH),8.14(d, J=8.4Hz, 1H, ArH); MS (ESI) m / z : 406.1[M+H] + .

Embodiment 2

[0067] Example 2: Synthesis of derivative b, i.e. (E)-2-(2,4-dihydroxyphenyl)vinyl-8-hydroxyquinoline

[0068] N 2 Add 810mg (2.00mmol) intermediate a and 15ml pyridine to a protected 100ml three-neck flask, dissolve, heat to reflux for 1 hour, add 5ml of distilled water, continue to reflux for 11 hours, cool, add 100ml of water, and use n-butanol (50ml×3 ), the organic layer was washed with distilled water (30 mL×2), washed with 30 mL of saturated brine, and the n-butanol layer was dried over anhydrous sodium sulfate overnight. Filtrate and evaporate the solvent under reduced pressure to obtain a crude product, which is separated by column chromatography, and the eluent is: chloroform / methanol ( V:V =9:1) to obtain 496 mg of reddish-brown derivative b with a yield of 89.0%. m.p. greater than 195-197°C; 1 HNMR (400MHz, CD 3 OD) δ: 6.34-6.38(m, 2H, ArH), 7.05(dd, J=7.2Hz, 1H, ArH), 7.26-7.34(m, 3H, ArH), 7.50(d, J=8.4Hz, 1H , ArH), 7.71(d, J=8.4Hz, 1H, ArH), 8.00(d, J=16....

Embodiment 3

[0070] The preparation method of various reagents in the analytical method of the present invention is:

[0071] (1) Preparation method of derivative b solution: weigh 2.8 mg of derivative b, dissolve in acetonitrile, and prepare a 100 mL solution with a concentration of 100 μmol L -1 .

[0072] (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;

[0073] (3) Fe 3+ Standard solution: weigh analytically pure Fe(NO 3 ) 3 9H 2 O 80.8mg, dissolved in double distilled water, and prepared into 100mL solution, Fe 3+ The concentration is 2.00×10 -3 mol L -1 ; Dilute step by step with twice distilled water to a suitable concentration as needed.

[0074] (4) Preparation of other coexisting ionic solutions: Take analytically pure nitrates...

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Abstract

The invention discloses a quinaldine derivative b fluorescent and colorimetric reagent as well as a preparation method and an application thereof and belongs to the field of organic synthesis and analytical chemistry. 8-hydroxyquinaldine serving as a raw material has a Knoevenagel condensation reaction with 2,4-dihydroxy benzaldehyde to obtain an intermediate a, wherein the chemical name of the intermediate a is (E)-2-(2,4-didiacetoxylphenyl)ethenyl-8-acetoxyquinoline; the intermediate a is hydrolyzed in a mixed medium of pyridine and water to obtain a derivative b, wherein the chemical name of the derivative b is (E)-2-(2,4-dihydroxylphenyl)ethenyl-8-hydroxyquinoline. The reaction materials are easily available; the synthesis method is simple; a target product can be obtained by two-step reaction. In a special solvent medium, the derivative b can act as fluorescent and colorimetric reagent for detecting Al<3+> and F-. The structural formula of the derivative is shown in the specification.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, in particular to a quinaldine derivative b fluorescence and colorimetric reagent, its preparation method and application. Background technique [0002] The analysis and detection of trace metals and non-metallic elements mostly use atomic emission, atomic absorption spectroscopy or traditional colorimetric spectrophotometry, polarography, ion chromatography, etc. Some techniques have low sensitivity, while others require larger analytical instruments or reagent consumption, greater pollution, and cumbersome operations. The fluorescent probe technology that has emerged in recent years uses the selective binding of probes to molecules and ions and the change of spectral characteristics, expresses molecular recognition information through fluorescent signals and color changes, and realizes in-situ real-time detection at the molecular level. Special effect recognition of met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26G01N21/64G01N21/31
CPCC07D215/26C09K11/06C09K2211/1007C09K2211/1029G01N21/31G01N21/643
Inventor 牟兰赵远会曾晞李俊
Owner GUIZHOU UNIV
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