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

A technology of triazene and quinoline, which is applied in the direction of chemical reaction of materials for analysis, fluorescence/phosphorescence, chemiluminescence/bioluminescence, etc., can solve the problems of triazene reagent interference, etc., and achieve high sensitivity and preparation Simple method and stable performance

Inactive Publication Date: 2010-06-23
SHANXI DATONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1) Diazotization of 8-aminoquinoline

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

[0022] 2) Preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0023] 0.25 g (0.00266 mol) of 2-aminopyridine was dissolved in 20 mL of ethanol, and the diazonium salt solution was slowly added with stirring at 0°C, during which the pH of the mixed solution was adjusted to 6 with saturated sodium carbonate solution, and the reaction was carried out for 2 hours. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, it was recrystallized twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 65%.

[0024] The product has been tested by elemental analysis, infrared spectroscopy and nuclear magnetic resonance spectr...

Embodiment 2

[0026] 1) Diazotization of 8-aminoquinoline

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

[0028] 2) Preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0029] 0.235 g (0.0025 mol) of 2-aminopyridine was dissolved in 20 mL of ethanol, and the diazonium salt solution was slowly added with stirring at 3° C., during which the pH value of the mixed solution was adjusted to 6.5 with saturated sodium acetate solution, and the reaction was carried out for 2.5 hours. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, it was recrystallized twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 60%.

[0030] After elemental analysis, infrared spectroscopy and nuclear magnetic resonance spectroscopy, it is ...

Embodiment 3

[0032] 1) Diazotization of 8-aminoquinoline

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

[0034] 2) Preparation of 1-(8-quinoline)-3-(2-pyridine)-triazene

[0035] 0.376 g (0.003 mol) of 2-aminopyridine was dissolved in 30 mL of ethanol, and the above diazonium salt solution was slowly added with stirring at 4°C, during which the pH of the mixed solution was adjusted to 7 with saturated sodium acetate solution, and the reaction was carried out for 2 hours. Let stand overnight, filter with suction, and wash with water and ethanol successively. After drying, it was recrystallized twice with 95% ethanol to obtain pure 1-(8-quinoline)-3-(2-pyridine)triazene (QPyT) with a yield of 50%.

[0036] The element analysis, infrared spectroscopy and nuclear magnetic resonance spectroscopy are consistent with...

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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 reagentwith 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 triazene compound containing a heterocyclic ring. The invention also relates to a preparation method and application of the compound. Background technique [0002] 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-section due to their strong electron donating or electron withdrawing ability (A. Abboto, L. Beverina) , R. Bozio, et al, Org. Lett. 2002, 4: 95-98). The triazene structure is easily coordinated with transition metal ions after being deprotonated, and is a good coordination group (J. Barker, ND Cameron, M. Kilner, et al, J. Chem. Soc. Dalton Trans, 1991, 12 :34-35), therefore, triazene reagent is an excellent color developer for metal ions such as cadmium, mercury, copper, nickel, silver, etc. Because of its high se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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