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Benzothiazole-triphenylamine dye with AIE effect and its preparation method and application

A technology of benzothiazole and triphenylamine, which is applied in the detection field of cyanide ions, can solve the problems of insensitive detection, complicated operation, high cost, etc., achieve high sensitivity, simple synthesis steps, and reduce detection cost

Active Publication Date: 2018-09-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of benzothiazole-triphenylamine dye with AIE effect and preparation method thereof, this dye aqueous solution can be high selectivity, high sensitivity, not interfered by other anions, detection limit is as low as ppm level, detects The method for detecting cyanide ion with low cost and convenient operation can overcome the problems of high cost, complicated operation and insensitive detection encountered in the field of cyanide ion detection

Method used

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  • Benzothiazole-triphenylamine dye with AIE effect and its preparation method and application
  • Benzothiazole-triphenylamine dye with AIE effect and its preparation method and application
  • Benzothiazole-triphenylamine dye with AIE effect and its preparation method and application

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Effect test

Embodiment 1

[0034] 1. The preparation method of benzothiazole-triphenylamine dye

[0035] Weigh 1.7422g benzothiazole-2-acetonitrile (10mmol) and 2.731g diphenylamino-4-benzaldehyde (10mmol) in a 100mL flask, add 50mL of dehydrated ethanol to dissolve, under the catalysis of 0.5mL ammonium acetate The reaction was stirred at room temperature for 24h. Then the crude product was obtained by filtration, and recrystallized from a dichloromethane (5 mL)-absolute ethanol (50 mL) mixed solution to obtain 3.125 g of a pure product in the form of an orange-red solid. Yield 73%.

[0036] 2. Compound Characterization

[0037] 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).

[0038] 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.

[0039] IR (cm -1 ,KBr):3750,3056,2360,2333,2205,1700,1566,1506,1482,1...

Embodiment 2

[0048] Detection of Cyanide Ions Using Dye

[0049] (1) Prepare a dye acetonitrile solution with a concentration of 1 mM, take 2 parts of 50 μL dye acetonitrile solution respectively, add distilled water to dilute to 10 mL, and obtain 2 parts of dye aqueous solution;

[0050] (2) preparation concentration is the tetra-n-butylammonium cyanide aqueous solution of 5mM, and concentration is the sodium sulfite aqueous solution of 5mM;

[0051] (3) In 2 parts of 10mL aqueous dye solution, add 0.1 mL each of tetra-n-butylammonium cyanide aqueous solution and sodium sulfite aqueous solution prepared in step (2) dropwise respectively. Fluorescence changes.

[0052] The results showed that the fluorescence of the dye aqueous solution was quenched after adding the aqueous solution of tetra-n-butylammonium cyanide, and the fluorescence of the aqueous dye solution remained unchanged after adding the aqueous solution of sodium sulfite. This shows that the dye of the present invention exhi...

Embodiment 3

[0054] Detection of Cyanide Ions Using Dye

[0055] (1) Prepare a dye DMSO solution with a concentration of 2 mM, take 2 parts of 50 μL of the dye DMSO solution, add distilled water to dilute to 10 mL, and obtain 2 parts of the dye aqueous solution;

[0056] (2) preparation concentration is the tetra-n-butylammonium cyanide aqueous solution of 10mM, and concentration is the sodium iodide aqueous solution of 10mM;

[0057] (3) Add 0.1 mL each of the tetra-n-butylammonium cyanide aqueous solution and sodium iodide aqueous solution prepared in step (2) dropwise to 2 parts of 10 mL dye aqueous solution respectively, after mixing evenly, observe the dye under 365nm light excitation Fluorescence changes in aqueous solutions.

[0058] The results showed that the fluorescence of the dye aqueous solution was quenched after adding the tetra-n-butylammonium cyanide aqueous solution, and the fluorescence of the dye aqueous solution remained unchanged after adding the sodium iodide aqueou...

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Abstract

The invention discloses benzothiazole-triphenylamine dye with an AIE effect and a preparation method and application thereof. The preparation method of the benzothiazole-triphenylamine dye comprises the steps that benzothiazole-2-acetonitrile and diphenyl amino-4-benzaldehyde are dissolved into absolute ethyl alcohol, ammonium acetate is added, and reacting under stirring is conducted at room temperature; a coarse product is obtained through filtering, and the pure benzothiazole-triphenylamine dye is obtained through recrystallization. According to the benzothiazole-triphenylamine dye, a cyanide ion detection method which is high in selectivity and sensitivity, is not disturbed by other negative ions, can achieve the detection limit as low as the ppm level and is low in detection cost and convenient and fast to operate can be achieved through an aqueous solution, and the problems that in the cyanide ion detection field, the cost is high, operation is complex, and detection is insensitive can be solved.

Description

Technical field: [0001] The invention relates to the detection of cyanide ions, in particular to a benzothiazole-triphenylamine compound with an AIE effect and a preparation method thereof, and a method for detecting cyanide ions using the dye, which is a kind of A fast and efficient dye for the detection of cyanide ions in aqueous solutions. technical background: [0002] In the fields of pharmaceuticals, health products, food, environmental science and industrial production, the detection of anions is widely involved. Among them, cyanide is an important raw material for synthetic resins, medicines, pesticides, insecticides, fertilizers, etc., and is widely used in various fields. However, cyanide is a highly toxic substance, and a small amount of cyanide ions can combine with ferric iron in cytochrome oxidase in the body, so that the cells lose the function of transporting oxygen, causing the body to suffer from hypoxia, poisoning and even death. The World Health Organiz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64C09K11/06
CPCC07D277/64C09K11/06
Inventor 瞿金清陈秀丽
Owner SOUTH CHINA UNIV OF TECH
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