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1-(8-chinoline)-3(2-pyridine)-triazene, preparation thereof and application thereof

A triazene and quinoline technology, which is applied in the direction of analysis, fluorescence/phosphorescence, chemiluminescence/bioluminescence, etc. by chemical reaction of materials, can solve the problems of large interference of triazene reagents, and achieve high sensitivity and selectivity. Good performance and low cost

Inactive Publication Date: 2008-10-01
SHANXI DATONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the triazene reagent is greatly interfered by coexisting ions, the selectivity needs to be improved.
[0003] At present, triazene reagents have been widely used as chromogenic reagents in UV-visible spectrophotometric analysis, but there are few reports on the use of triazene reagents as fluorescent reagents for the fluorescence detection of metal ions

Method used

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  • 1-(8-chinoline)-3(2-pyridine)-triazene, preparation thereof and application thereof
  • 1-(8-chinoline)-3(2-pyridine)-triazene, preparation thereof and application thereof
  • 1-(8-chinoline)-3(2-pyridine)-triazene, preparation thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1), the diazotization of 8-aminoquinoline

[0021] Dissolve 0.36g (0.0025mol) of 8-aminoquinoline in 0.5mL of formic acid and 2.5mL of concentrated sulfuric acid, slowly add 2.5mL of 0.069g / mL sodium nitrite aqueous solution at 0°C under stirring, and react for 30min to make the diazo complete.

[0022] 2), the preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0023] Dissolve 0.25g (0.00266mol) of 2-aminopyridine in 20mL of ethanol, slowly add the above diazonium salt solution under stirring at 0°C, adjust the pH of the mixture to 6 with saturated sodium carbonate solution, and react for 2h. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, recrystallize twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 65%.

[0024] The product was tested by elemental analysis, infrared spectrum and nuclear magnetic resonance spectrum, and it was consistent with the target pr...

Embodiment 2

[0026] 1), the diazotization of 8-aminoquinoline

[0027] Dissolve 0.576g (0.004mol) of 8-aminoquinoline in 2.0mL of acetic acid and 2.5mL of concentrated sulfuric acid, slowly add 3.0mL of 0.069g / mL sodium nitrite aqueous solution at 2°C under stirring, and react for 40min to make the diazo complete.

[0028] 2), the preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0029] Dissolve 0.235g (0.0025mol) of 2-aminopyridine in 20mL of ethanol, slowly add the above diazonium salt solution under stirring at 3°C, adjust the pH of the mixture to 6.5 with saturated sodium acetate solution, and react for 2.5h. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, recrystallize twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 60%.

[0030] The elemental analysis, infrared spectrum and nuclear magnetic resonance spectrum test are consistent with the target product.

Embodiment 3

[0032] 1), the diazotization of 8-aminoquinoline

[0033] Dissolve 0.432g (0.004mol) of 8-aminoquinoline in 1.5mL of formic acid and 5.0mL of concentrated sulfuric acid, slowly add 3.0mL of 0.069g / mL sodium nitrite aqueous solution at 0°C under stirring, and react for 50min to make the diazo complete.

[0034] 2), the preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0035] Dissolve 0.376g (0.003mol) of 2-aminopyridine in 30mL of ethanol, slowly add the above-mentioned diazonium salt solution under stirring at 4°C, adjust the pH of the mixture to 7 with saturated sodium acetate solution, and react for 2h. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, recrystallize twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 50%.

[0036] The elemental analysis, infrared spectrum and nuclear magnetic resonance spectrum test are consistent with the target product.

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Abstract

The invention relates to a triazene compound 1-(8-quinoline)-3-(2-pyridyl)-triazene (QPyT) which contains heterocycle. The preparation method of the invention comprises the steps: diazotizing 8-amino quinoline by using sodium nitrate under acidic condition and reacting with 2-aminopyridine in alcoholic solution. The compound is not only a good visualization reagent, but also a fluorescent reagent with high sensitivity and good selectivity, which can be used for fluoroscopic examination of metal ion, in particular for the examination of Pb (II) in alkaline medium.

Description

technical field [0001] The invention relates to a fluorescent reagent, in particular to a heterocyclic-containing triazene compound, and also relates to a preparation method and application of the compound. Background technique [0002] Due to their strong electron-donating or electron-withdrawing capabilities, organic heterocyclic structures are considered to be effective structures for designing and synthesizing organic molecules with strong two-photon-induced upconversion fluorescence and large two-photon absorption cross-sections (A.Abboto, L.Beverina , R. Bozio, et al, Org. Lett. 2002, 4:95-98). After the deprotonation of the triazene structure, it is easy to coordinate with transition metal ions and is a good coordination group (J.Barker, N.D.Cameron, M.Kilner, et al, J.Chem.Soc.Dalton Trans, 1991, 12 : 34-35), therefore, triazene reagent is the excellent color developer of metal ions such as cadmium, mercury, copper, nickel, silver, because of its advantages such as ...

Claims

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Application Information

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IPC IPC(8): C07D401/12G01N21/64G01N21/76
Inventor 冯锋王诚陈泽忠卢珍孟双明
Owner SHANXI DATONG UNIV
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