Bis(8-quinoline diazo amido)-biphenyl, preparation method and application thereof

A technology of nitrogen amino and quinoline, which is applied in the field of derivatives containing bistriazene structure, can solve the problems of triazene reagent interference, etc., and achieve the effects of low cost, enlarged conjugated system, and stable performance

Inactive Publication Date: 2008-09-24
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.
[0004] At present, triazene reagent has been widely used in UV-visibl...

Method used

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  • Bis(8-quinoline diazo amido)-biphenyl, preparation method and application thereof
  • Bis(8-quinoline diazo amido)-biphenyl, preparation method and application thereof
  • Bis(8-quinoline diazo amido)-biphenyl, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1), the diazotization of 8-aminoquinoline

[0023] Add 2mL of concentrated hydrochloric acid and 0.288g (0.002mol) of 8-aminoquinoline into the flask, slowly add 2mL of 0.069g / mL sodium nitrite aqueous solution under stirring at 2°C, and accelerate the stirring reaction for 2h to complete the diazotization.

[0024] 2), the preparation of two (8-quinoline diazoamino)-biphenyl

[0025] Dissolve 0.184g (0.001mol) of benzidine in 10mL of ethanol, slowly add the above diazonium salt solution under stirring at 0°C, and adjust the pH of the mixture to 7 with saturated sodium carbonate solution, and react for 2h. Let stand overnight, filter with suction, and wash with water and ethanol solution successively. After drying, recrystallize twice with 95% ethanol to obtain 0.346 g of pure bis(8-quinolinediazoamino)-biphenyl (BQDADB) with a yield of 70%.

[0026] The product was tested by elemental analysis, infrared spectrum and nuclear magnetic resonance spectrum, and it was con...

Embodiment 2

[0028] 1), the diazotization of 8-aminoquinoline

[0029] Add 5mL of a mixed solution of concentrated hydrochloric acid and phosphoric acid, 5mL of water, 0.288g (0.002mol) of 8-aminoquinoline into the flask, slowly add 4mL of 0.069g / mL sodium nitrite aqueous solution under stirring at 0°C, and accelerate the stirring reaction for 2.5h , so that the diazotization is complete.

[0030] 2), the preparation of two (8-quinoline diazoamino)-biphenyl

[0031] Dissolve 0.184g (0.001mol) of benzidine in 10mL of ethanol, slowly add the above diazonium salt solution under stirring at 2°C, adjust the pH of the mixture to 6 with saturated sodium carbonate solution, and react for 2.5h. Let stand overnight, filter with suction, and wash with water and ethanol solution successively. After drying, recrystallize twice with 95% ethanol to obtain 0.386 g of pure bis(8-quinolinediazoamino)-biphenyl (BQDADB) with a yield of 78%.

[0032] The product was tested by elemental analysis, infrared sp...

Embodiment 3

[0034] 1), the diazotization of 8-aminoquinoline

[0035] Add 4mL of concentrated sulfuric acid, 4mL of water, 0.288g (0.002mol) of 8-aminoquinoline into the flask, slowly add 2.5mL of 0.069g / mL sodium nitrite aqueous solution under stirring at 3°C, accelerate the stirring reaction for 1.5h, and make the diazo complete.

[0036] 2), the preparation of two (8-quinoline diazoamino)-biphenyl

[0037] Dissolve 0.184g (0.001mol) of benzidine in 20mL of ethanol, slowly add the above diazonium salt solution under stirring at 0°C, and adjust the pH of the mixture to 6 with saturated sodium carbonate solution, and react for 1.5h. Let stand overnight, filter with suction, and wash with water and ethanol solution successively. After drying, recrystallize twice with 95% ethanol to obtain 0.3 g of pure bis(8-quinolinediazoamino)-biphenyl (BQDADB) with a yield of 60%.

[0038] The product was tested by elemental analysis, infrared spectrum and nuclear magnetic resonance spectrum, and it ...

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Abstract

The present invention relates to a heterocyclic di-triazene compound, di-(8-quinoline diazoaminoazobenzene)-biphenyl (BQDADB). 8-aminoquinoline is treated through diazotization by sodium nitrite under the acidic conditions and then reacts with benzidine in the alcohol solution; thus the compound can be prepared. The compound can not only be used as an excellent chromogenic agent, but also can be used as a fluorescent reagent with high sensitivity and high selectivity. And the compound can be used for testing the fluorescence of metal ions, in particular testing the Cu(II) in the alkaline medium.

Description

technical field [0001] The invention relates to a fluorescent reagent, in particular to a derivative of a heterocyclic triazene compound, especially a derivative containing a bistriazene structure. The invention also relates to the 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). [0003] After the triazene structure is deprotonated, 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 an excellent color developer for metal ions suc...

Claims

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Application Information

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IPC IPC(8): C07D215/40G01N21/64G01N21/76
Inventor 冯锋王诚陈泽忠卢珍孟双明
Owner SHANXI DATONG UNIV
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