Preparation and application of coumarin 2-hydrazinobenzothiazole Schiff base Cd<2+> fluorescent probe

A technology of benzothiazole and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of poor selectivity and achieve the effects of low detection limit, high anti-interference ability and high sensitivity

Inactive Publication Date: 2018-08-17
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Fluorescence probe assay in Cd 2+ Detection has also been favored by the majority of analysts, but for Cd 2+ The identified fluorescence recognition is often affected by the Zn 2+ interference, but there is a defect of poor selectivity

Method used

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  • Preparation and application of coumarin 2-hydrazinobenzothiazole Schiff base Cd&lt;2+&gt; fluorescent probe
  • Preparation and application of coumarin 2-hydrazinobenzothiazole Schiff base Cd&lt;2+&gt; fluorescent probe
  • Preparation and application of coumarin 2-hydrazinobenzothiazole Schiff base Cd&lt;2+&gt; fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1), the reaction formula of synthetic 7-hydroxyl-8-coumarin aldehyde:

[0036]

[0037] (2), the specific steps of synthetic 7-hydroxyl-8-coumarin aldehyde:

[0038] Weigh 10g of 7-hydroxycoumarin and 20g of hexamethylenetetramine and dissolve in 75mL of glacial acetic acid, stir and heat to 90°C and react for 8h, then add hydrochloric acid (150mL, conc.HCl / H 2 O=84:100, v / v) and stirred at 70°C for 30min. Cool, add ice water, extract with ethyl acetate, then dry the organic phase with anhydrous sodium sulfate, filter under reduced pressure, and remove the solvent by rotary evaporation of the filtrate under reduced pressure to obtain a yellow solid. Then recrystallize with absolute ethanol to obtain 7-hydroxyl-8-coumarin aldehyde. The yield is 18%.

[0039] (3), the reaction formula of synthesizing 2-hydrazinobenzothiazole:

[0040]

[0041] (4), the specific steps of synthetic 2-hydrazinobenzothiazole:

[0042] Add 2.00g of 2-aminobenzothiazole, 2.50g of 80...

Embodiment 2

[0058] (1), the specific steps of synthetic 7-hydroxyl-8-coumarin aldehyde:

[0059] Weigh 10g of 7-hydroxycoumarin and 20g of hexamethylenetetramine and dissolve in 75mL of glacial acetic acid, stir and heat to 70°C and react for 8h, then add hydrochloric acid (150mL, conc.HCl / H 2 O=84:100, v / v) and stirred at 50°C for 30min. Cool, add ice water, extract with ethyl acetate, then dry the organic phase with anhydrous sodium sulfate, filter under reduced pressure, and remove the solvent by rotary evaporation of the filtrate under reduced pressure to obtain a yellow solid. Then recrystallize with absolute ethanol to obtain 7-hydroxyl-8-coumarin aldehyde. The yield was 13%.

[0060] (2), the specific steps of synthetic 2-hydrazinobenzothiazole:

[0061] Add 2.00g of 2-aminobenzothiazole, 2.50g of 80% hydrazine hydrate, 2.66mL of concentrated hydrochloric acid, and 20.00mL of absolute ethanol into a 50mL three-neck flask, and heat the mixed solution to 120°C under the protection...

Embodiment 3

[0065] (1), the specific steps of synthetic 7-hydroxyl-8-coumarin aldehyde:

[0066] Weigh 10g of 7-hydroxycoumarin and 20g of hexamethylenetetramine and dissolve in 75mL of glacial acetic acid, stir and heat to 100°C and react for 8h, then add hydrochloric acid (150mL, conc.HCl / H 2 O=84:100, v / v) and stirred at 90°C for 30min. Cool, add ice water, extract with ethyl acetate, then dry the organic phase with anhydrous sodium sulfate, filter under reduced pressure, and remove the solvent by rotary evaporation of the filtrate under reduced pressure to obtain a yellow solid. Then recrystallize with absolute ethanol to obtain 7-hydroxyl-8-coumarin aldehyde. The yield is 15%.

[0067] (2), the specific steps of synthetic 2-hydrazinobenzothiazole:

[0068] Add 2.00g of 2-aminobenzothiazole, 2.50g of 80% hydrazine hydrate, 2.66mL of concentrated hydrochloric acid, and 20.00mL of absolute ethanol into a 50mL three-neck flask, and heat the mixed solution to 110°C under the protection...

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Abstract

The invention relates to the field of fluorescent probes, and in particular relates to a coumarin 2-hydrazinobenzothiazole Schiff base fluorescent probe and an application thereof. The fluorescent probe has a specific structure shown in the description. The fluorescent probe provided by the invention can recognize Cd<2+> in an EtOH-H2O (95:5, v / v, and HEPES 20 mmol / L) solution, and has the advantages of exhibiting excellent selectivity in competition with other ions, and having higher fluorescence sensing properties, low detection limit, high detection sensitivity and a high fluorescence quantum yield.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a coumarin 2-hydrazinobenzothiazole Schiff base fluorescent probe and its application. Background technique [0002] traditional for cd 2+ The detection methods include atomic absorption method, plasma emission spectrometry, electrochemical analysis method and so on. In recent years, due to the remarkable advantages of convenient operation, low cost, high selectivity, and high sensitivity, fluorescent probe technology has attracted extensive attention in the detection of metal ions. Fluorescence probe assay in Cd 2+ Detection has also been favored by the majority of analysts, but for Cd 2+ The identified fluorescence recognition is often affected by the Zn 2+ interference, but there is a defect of poor selectivity. Therefore, a kind of Cd was designed and synthesized 2+ Small molecule fluorescent probes with specific recognition have important practical value. [0003] Sc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C09K11/06G01N21/64
CPCC07D417/12C09K11/06C09K2211/1037C09K2211/1088G01N21/643
Inventor 汤艳峰黄洋朱金丽孙同明王淼万永兴施安霁
Owner NANTONG UNIVERSITY
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