Iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole and preparation method and application thereof

A technology of methylbenzothiazole and naphthopyran, which is applied in the field of anion detection, can solve the problems of low fluorescence emission peak, complex receptor structure, and restricted application, and achieves easy-to-obtain raw materials, great application value, and simple synthesis method Effect

Inactive Publication Date: 2017-06-09
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
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  • Claims
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Problems solved by technology

At present, the literature has disclosed a variety of receptors for colorimetric or fluorescent detection of cyanide ions, but these receptors are often complex in structure and difficult to synthesize
Literature 1 reported a double-Schiff base cyanide sensor containing phenolic hydroxyl groups, the sensor molecule can be sensitive to CN in acetonitrile solvent - Selective fluorescence recognition is achieved, but the fluorescence emission

Method used

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  • Iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole and preparation method and application thereof
  • Iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole and preparation method and application thereof
  • Iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0032] 2. CN - Preparation and detection of ion detection test paper

[0033] Based on the cyanide ion detection test paper of iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl)benzothiazole, the specific preparation method is as follows:

[0034] First, use 0.1~0.5mol L of filter paper -1 Soak in dilute hydrochloric acid for 0.5 to 1 hour, and wash with distilled water until the filtrate is neutral; remove water by suction filtration, and place the filter paper in a vacuum drying box to dry; then iodide the acceptor compound-N-ethyl- 2-(2-H-Naphthopyran-3-vinyl)benzothiazole was dissolved in HEPES-DMSO-H 2 O system (DMSO:H 2 O=1 / 1 (v / v), HEPES: 0.008~0.012M, pH=7.2~7.4), the concentration is 1.0~2.0×10 -3 mol·L -1 The solution was then added dropwise to the treated filter paper to make the HEPES-DMSO-H of the acceptor compound 2 The O solution system is uniformly adsorbed on the filter paper; then the filter paper is dried in a vacuum drying box, and finally cut into 2cm × 2cm...

Example Embodiment

[0039] Example 1

[0040] 2-H-Naphthopyran-3-carbaldehyde (2 mmol) and quaternary ammonium salt of methylbenzothiazole (2.2 mmol) were mixed in absolute ethanol (20 mL), piperidine (0.04 mmol) was added, and the mixture was stirred and refluxed After 6h, the reaction was cooled and suction filtered to obtain a dark green solid, which was rinsed with absolute ethanol for several times to obtain the product iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole.

[0041] Yield: Yield 78%, m.p.261-263°C; 1 H NMR(500MHz, DMSO)δ8.45(d,J=8.0Hz,1H),8.34(s,1H),8.28(d,J=8.5Hz,1H),8.20(d,J=8.5Hz,1H) ), 8.09(d, J=15.6Hz, 1H), 7.98(d, J=8.8Hz, 1H), 7.93(d, J=8.1Hz, 1H), 7.88(t, J=7.5Hz, 1H), 7.79(t,J=7.6Hz,1H),7.66(t,J=7.6Hz,1H),7.48(t,J=7.5Hz,1H),7.36(d,J=15.6Hz,1H),7.24( d, J=8.9Hz, 1H), 5.40 (s, 2H), 4.92 (q, J=7.1Hz, 2H), 1.06 (t, J=7.0Hz, 3H). 13 C NMR(126MHz,DMSO)δ171.45,155.04,146.52,141.51,133.93,133.39,130.56,130.02,129.58,128.75,128.52,128.46,125.19,124.93,122.00,117.86,...

Example Embodiment

[0042] Example 2

[0043] 2-H-Naphthopyran-3-carbaldehyde (2 mmol) and quaternary ammonium salt of methylbenzothiazole (2.0 mmol) were mixed in absolute ethanol (20 mL), piperidine (0.04 mmol) was added, and the mixture was stirred and refluxed After 6h, the reaction was cooled and suction filtered to obtain a dark green solid, which was rinsed with absolute ethanol for several times to obtain the product iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole.

[0044] Yield: 78%. The characterization data of the synthesized product are the same as those in Example 1.

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Abstract

The invention discloses iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole, a preparation method and application thereof in detecting cyanide ions. The iodide-N-ethyl-2-(2-H-naphthopyran-3-vinyl) benzothiazole adopts naphthopyran as an electron-donating group, adopts quaternary ammonium salt of benzothiazole as an electron-withdrawing group, and adopts C=C double bonds as a reactive combination site, the cyanide ions can have an additive reaction with the C=N double bonds of the benzothiazole in a receptor molecule, thus leading to the blocking of charge transfer in the receptor molecule, so that the receptor molecule is varied in color and fluorescence. An effect of the compound on identifying negative ions such as CN-F-, Cl-, Br-, I-, Ac-, H2PO4-, HSO4-, ClO4-, S2-, SCN- and the like is researched by virtue of a colorimetric method, ultraviolet-visible absorption spectrometry and a fluorescent spectrometry, the receptor compound can independently and selectively identify the cyanide ions in a HEPES-DMSO-H2O system, the minimum detection limit can reach 2.9*10<-7> mol.L<-1>, and the application value in detecting the cyanide in drinking water is great.

Description

technical field [0001] The invention belongs to the technical field of anion detection, and relates to a near-infrared acceptor compound for detecting cyanide, in particular to a compound based on iodide-N-ethyl-2-(2-H-naphthopyran-3- Vinyl) cyanide acceptor compound and preparation method of benzothiazole and its application in CN - application in detection. Background technique [0002] Cyanide is one of the most potent and fastest-acting poisons known. Cyanides are mainly divided into inorganic cyanides and organic cyanides. In daily life, cyanide is contained in foods such as cassava and bitter almonds, and car exhaust and cigarette smoke from human activities also contain cyanide. Cyanide is easily absorbed by the human body and can enter the human body through the mouth, respiratory tract or skin. When cyanide enters the stomach, under the dissociation of gastric acid, it can be immediately hydrolyzed into HCN and absorbed. After HCN enters the blood circulation, t...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64G01N21/78
CPCC07D417/06C09K11/06C09K2211/1037C09K2211/1088G01N21/64G01N21/78
Inventor 董伟李军舰魏威齐晓亮
Owner NANJING UNIV OF SCI & TECH
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