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Benzothiazole 2-acetonitrile dye and application thereof

A technology of benzothiazole and acetonitrile, applied in styryl dyes, organic dyes, methine/polymethine dyes, etc., can solve the problems of easy quenching and lack of aggregation-induced luminescence effect.

Inactive Publication Date: 2016-12-07
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned 2-hydroxyphenyl-benzothiazole derivatives are easy to quench fluorescence in aqueous solution, and do not have aggregation-induced luminescent effect

Method used

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  • Benzothiazole 2-acetonitrile dye and application thereof
  • Benzothiazole 2-acetonitrile dye and application thereof
  • Benzothiazole 2-acetonitrile dye and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Preparation of benzothiazole 2-acetonitrile dyes

[0026] Add 2.73g (10mmol) 4-(diphenylamine) benzaldehyde, 1.74g (10mmol) benzothiazole 2-acetonitrile-2-acetonitrile and 0.77g (10mmol) ammonium acetate in a 50mL flask, and then add 20mL absolute ethanol. After reacting overnight at room temperature, the precipitate was filtered and recrystallized in ethanol to obtain 3.56 g of an orange-red solid. Yield 83%.

[0027] 2. Compound Characterization

[0028] 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.01(s,1H),7.94(d,1H),7.78(t,3H),7.39(t,1H),7.25(m,5H),7.08(m,6H),6.93( d, 2H).

[0029] 13 C NMR (100MHz, CDCl 3 )δ(ppm):163.91,153.75,151.58,146.18,145.98,134.79,132.26,129.78,126.75,126.30,125.49,125.23,124.47,123.16,121.59,119.72,117.55,100.71,77.43,77.12,76.80.

[0030] IR (cm -1 ,KBr):3750,3056,2360,2333,2205,1700,1566,1506,1482,1426,1331,1295,1164,1069,980,914,819,754,724,700,617,587,533,498

[0031] HR-MS (ESI): C 28 h 19 N 3 S m / z,429for[M+Na] + :452.1203

[0...

Embodiment 2

[0035] Embodiment 2 (fluorescent properties of benzothiazole 2-acetonitrile dyes)

[0036]Prepare 5 mM benzothiazole 2-acetonitrile dye DMSO solution, take 10 μL benzothiazole 2-acetonitrile dye DMSO solution, add 10 mL volumetric flask, add 1, 2, 3, 4, 5, 6, 7 , 8, 9mL of distilled water, and then add DMSO to adjust the volume of the solution to 10mL to obtain a benzothiazole 2-acetonitrile dye water / DMSO solution (9 / 1, v / v) with a concentration of 1 μM and a benzothiazole with a concentration of 5 μM 2-acetonitrile dye water / DMSO solution (8 / 2, v / v), the concentration of benzothiazole 5 μM 2-acetonitrile dye water / DMSO solution (7 / 3, v / v), the concentration of 5 μM benzene Benzothiazole 2-acetonitrile dye water / DMSO solution (6 / 4, v / v), the concentration is 5 μM Benzothiazole 2-acetonitrile dye water / DMSO solution (5 / 5, v / v), the concentration is 5 μM The benzothiazole 2-acetonitrile dye water / DMSO solution (4 / 6, v / v), the concentration of 5 μM benzothiazole 2-acetonitrile ...

Embodiment 3

[0044] The following benzothiazole 2-acetonitrile dyes represented by the chemical formula (I) are used as fluorescent probes for detecting cyanide ions.

[0045] 1. Fluorescent detection of cyanide ion

[0046] 1. Selectivity of Fluorescent Detection of Cyanide Ion

[0047] (1) Prepare an acetonitrile solution of benzothiazole 2-acetonitrile dye with a concentration of 5 mM.

[0048] (2) Prepare NaF, NaCl, KBr, KI, tetra-n-butylammonium cyanide, CH 3 COONa,NaNO 3 , Na 2 SO 4 ,NaHSO 4 ,NaHSO 3 ,NaH 2 PO 4 of aqueous solution.

[0049] (3) Take 10 μL of benzothiazole 2-acetonitrile dye acetonitrile solution, add dropwise NaF, NaCl, KBr, KI, tetra-n-butylammonium cyanide, CH 3 COONa,NaNO 3 , Na 2 SO 4 ,NaHSO 4 ,NaHSO 3 ,NaH 2 PO 4 10 μL of the aqueous solution of benzothiazole 2-acetonitrile dye was diluted to 10 mL with water, and the fluorescence change of the benzothiazole 2-acetonitrile dye aqueous solution was observed under the excitation of 365 nm light. ...

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Abstract

The invention relates to benzothiazole 2-acetonitrile dye. A chemical structure of the benzothiazole 2-acetonitrile dye is shown as a formula (I) in the specification. The benzothiazole 2-acetonitrile dye is prepared from 4-(diphenylamine) benzaldehyde and benzothiazole 2-acetonitrile-2-acetonitrile through a reaction. The benzothiazole 2-acetonitrile dye can be used for detecting cyanide ions.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to benzothiazole 2-acetonitrile compounds, in particular to benzothiazole 2-acetonitrile fluorescent probes and applications thereof. Background technique [0002] Anions play an important role in environmental protection, industrial production and biological applications. Among them, cyanide ion is one of the most toxic anions. It enters the human body through the lungs, stomach or skin, causing vomiting, convulsions, loss of consciousness and even death. An extremely small amount of cyanide ion can cause death in a few minutes. Therefore, methods for efficient detection of cyanide ions are attractive. Therefore, exploring fluorescent probes with high selectivity and sensitivity has aroused the interest of many researchers. For example, Jo TG et al. have synthesized dyes containing salicylaldehyde and maleic nitrile, which can detect cyanide ions and copper ions in different solven...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C09K11/06G01N21/64C07D277/64
CPCC09B23/146C09K11/06C09K2211/1014C09K2211/1037G01N21/64G01N21/6428G01N21/643G01N2021/6432
Inventor 刘瑞源严轶琛路新卫游文伟
Owner SOUTHERN MEDICAL UNIVERSITY
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