1,8-bis(2-benzothiazolydiazoamino)- naphthaline, preparation and application thereof

A diazoamino and benzothiazole technology, 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 and achieve high sensitivity, The preparation method is simple and the selectivity is good

Inactive Publication Date: 2012-09-05
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.
[0004] At present, triazene reagent has been widely used in UV-visible spectrophotometric analysis as a chromogenic reagent, but there are few reports on using it as a coordination structure of a fluorescent reagent for the fluorescence detection of metal ions

Method used

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  • 1,8-bis(2-benzothiazolydiazoamino)- naphthaline, preparation and application thereof
  • 1,8-bis(2-benzothiazolydiazoamino)- naphthaline, preparation and application thereof
  • 1,8-bis(2-benzothiazolydiazoamino)- naphthaline, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1), the diazotization of 2-aminobenzothiazole

[0024] Add 1mL of formic acid, 3mL of water, 2mL of concentrated sulfuric acid and 0.6g (0.004mol) of 2-aminobenzothiazole to the flask in sequence, slowly add 2mL of 0.14g / mL sodium nitrite aqueous solution under stirring at 3°C, and react for 30min to make the diazo complete.

[0025] 2), the preparation of 1,8-bis(2-benzothiazolediazoamino)naphthalene

[0026] Dissolve 0.316g (0.002mol) of 1,8-naphthalenediamine 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 sodium acetate solution, react for 2 hours, and store in the refrigerator Stand overnight, filter with suction, and wash with 50% aqueous ethanol. After drying, it was applied to a chromatographic column and separated by column chromatography using ethyl acetate:petroleum ether=2:3 (volume ratio) as the eluent, and then recrystallized with 95% ethanol to obtain a black pure product.

...

Embodiment 2

[0029] 1), the diazotization of 2-aminobenzothiazole

[0030] Add 2mL of formic acid, 4mL of water, 3mL of concentrated sulfuric acid, 1mL of phosphoric acid and 0.75g (0.005mol) of 2-aminobenzothiazole in the flask, and slowly add 3mL of 0.14g / mL sodium nitrite aqueous solution at 2°C under stirring. React for 40 minutes to complete the diazotization.

[0031] 2), the preparation of 1,8-bis(2-benzothiazolediazoamino)naphthalene

[0032] Dissolve 0.316g (0.002mol) of 1,8-naphthalenediamine in 25mL of ethanol, slowly add the above diazonium salt solution under stirring at 3°C, adjust the pH of the mixture to 7 with sodium acetate solution, react for 2.5h, and Let stand overnight in the refrigerator, filter with suction, and wash with 50% aqueous ethanol. After drying, it was applied to a chromatographic column and separated by column chromatography using ethyl acetate:petroleum ether=2:3 (volume ratio) as the eluent, and then recrystallized with 95% ethanol to obtain a black ...

Embodiment 3

[0034] 1), the diazotization of 2-aminobenzothiazole

[0035] Add 2.5mL of acetic acid, 6mL of water, 4mL of concentrated sulfuric acid and 0.675g (0.0045mol) of 2-aminobenzothiazole in sequence in the flask, and slowly add 3.5mL of 0.14g / mL sodium nitrite aqueous solution at 3°C ​​under stirring, and react 40min to complete the diazotization.

[0036] 2), the preparation of 1,8-bis(2-benzothiazolediazoamino)naphthalene

[0037] Dissolve 0.474g (0.003mol) of 1,8-naphthalenediamine in 30mL of ethanol, slowly add the above diazonium salt solution under stirring at 3°C, adjust the pH of the mixture to 5 with saturated sodium carbonate solution, and react for 1.6h. Stand overnight in the refrigerator, filter with suction, and wash with 50% aqueous ethanol. After drying, it was applied to a chromatographic column and separated by column chromatography using ethyl acetate:petroleum ether=2:3 (volume ratio) as the eluent, and then recrystallized with 90% ethanol to obtain a black p...

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Abstract

The invention relates to a heterocyclic ditriazene compound 1, 8-di(2-benzothiazole diazoamino) albocarbon(BBTANP). The preparation of the invention comprises the steps of diazotizing 2-aminobenzothiazole by using sodium nitrate under acidic condition, reacting with 1, 8-Naphthalenediamine 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, especially for the examination of Cu (II) in 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). And the introduction of benzothiazole structure has a wide range of applications in the construction of fluorescent organic molecules. [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.K...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/82G01N21/64G01N21/76
Inventor 冯锋付国良陈泽忠白云峰孟双明
Owner SHANXI DATONG UNIV
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