Cyanide receptor compound based on 2-cyano-3-(6-N, N-dimethylamino-2-naphthyl) acrylonitrile, preparation method and application

A technology of dimethylammonia and compounds, which is applied in the field of anion detection, can solve the problems of complex receptor structure, difficulty in synthesis, and restrictions on the application of detection and identification of cyanide ions, and achieve the effect of easy-to-obtain raw materials and simple synthesis

Active Publication Date: 2015-11-11
NANJING UNIV OF SCI & TECH
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  • Description
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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. However, these receptors are often

Method used

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  • Cyanide receptor compound based on 2-cyano-3-(6-N, N-dimethylamino-2-naphthyl) acrylonitrile, preparation method and application
  • Cyanide receptor compound based on 2-cyano-3-(6-N, N-dimethylamino-2-naphthyl) acrylonitrile, preparation method and application
  • Cyanide receptor compound based on 2-cyano-3-(6-N, N-dimethylamino-2-naphthyl) acrylonitrile, preparation method and application

Examples

Experimental program
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preparation example Construction

[0033] (2) CN - Preparation of ion detection test paper

[0034] For convenient and quick detection of CN - , the present invention has prepared the cyanide detection test paper based on this acceptor. The specific preparation method is as follows:

[0035] First filter paper with 0.1 ~ 0.5mol L -1 Soak in dilute hydrochloric acid for 0.5 to 1 hour, wash with distilled water until the filtrate is neutral; remove the water by suction filtration, and dry the filter paper in a vacuum oven; then dissolve the acceptor compound in HEPES-DMSO- h 2 In O system, the concentration is 1.0~2.0×10 -3 mol L -1 The solution was added dropwise to the treated filter paper to make the HEPES-DMSO-H of the acceptor compound 2 The O solution system is evenly adsorbed on the filter paper; then the filter paper is dried in a vacuum oven, and finally cut into 2cm×2cm test paper pieces to obtain CN - Ion detection test paper.

[0036] Cyanide detection test paper detection CN - The method is a...

Embodiment 1

[0041] 1. Receptor synthesis

[0042] Mix 6-dimethylamino-2-naphthaldehyde (2mmol) and malononitrile (2.2mmol) in absolute ethanol (20mL), add piperidine (0.04mmol), stir at room temperature for 3h, cool down after the reaction After suction filtration, a red solid was obtained, which was washed several times with absolute ethanol to obtain the product—2-cyano-3-(6-N,N-dimethylamino-2-naphthyl)acrylonitrile.

[0043] Yield: 82.0% (m.p.170℃~172℃), IR: (KBr,cm -1 )v: 2213(-CN), 1619(C=C). 1 HNMR (500MHz, DMSO) δ8.37(s, 1H), 8.24(s, 1H), 7.95(d, J=8.8Hz, 1H), 7.85(d, J=9.2Hz, 1H), 7.73(dd, J=12.5,6.2Hz,1H),7.30(dd,J=9.2,2.4Hz,1H),6.98(d,J=1.9Hz,1H),3.12(s,6H). 13 CNMR (DMSO-d 6 ,125MHz):δ160.9,151.7,138.4,136.3,131.7,127.5,127.3,124.8,124.6,117.3,115.9,115.0,105.4,75.9,40.88,40.82; MSm / z[M] + Calcd for C 16 h 13 N 3 247.1, found 247.4.

[0044] 2. CN - Preparation and detection of test paper

[0045] (1) CN - Preparation of test paper: cut the filter paper into a squa...

Embodiment 2

[0048] 1. Mix 6-dimethylamino-2-naphthaldehyde (2mmol) and malononitrile (2mmol) in absolute ethanol (20mL), add piperidine (0.04mmol), stir at room temperature for 3h, after the reaction After cooling and suction filtration, a red solid was obtained, which was rinsed several times with absolute ethanol to obtain the product—2-cyano-3-(6-N,N-dimethylamino-2-naphthyl)acrylonitrile.

[0049] Yield: 80%. The characterization data of the synthesized product are the same as in Example 1.

[0050] 2. CN - Preparation and detection of detection test paper: same as embodiment 1.

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Abstract

The invention discloses a cyanide receptor compound based on 2-cyano-3-(6-N, N-dimethylamino-2-naphthyl) acrylonitrile, a preparation method and application thereof. The compound takes a C=C double bond as a reactive binding site and takes 6-N, N-dimethylamino-2-naphthaldehyde as a fluorescence signal reporter group. When a receptor encounters cyanide ions, the cyanide ions and the C=C double bond of the receptor can carry out addition reaction so as to cause proton transfer and charge transfer in receptor molecules, so that the receptor molecules have color and fluorescence changes. The invention respectively researches the identification effects of the compound to F<->, Cl<->, Br<->, I<->, Ac<->, H2PO4<->, HSO4<->, ClO4<-> and CN<-> through colorimetry, ultraviolet-visible absorption spectroscopy and fluorescent spectrometry. The results show that the receptor compound can singly and selectively identify cyanide ions in an HEPES-DMSO-H2O system and has very high sensitivity to detection of CN<->.

Description

technical field [0001] The invention belongs to the technical field of anion detection, and relates to an acceptor compound for detecting cyanide, in particular to a 2-cyano-3-(6-N,N-dimethylamino-2-naphthyl)-based Cyanide acceptor compound of acrylonitrile, preparation method and its detection of CN - in the application. Background technique [0002] Cyanide is one of the strongest and fastest-acting poisons known to man. Cyanides are mainly divided into inorganic cyanides such as hydrocyanic acid and potassium cyanide, and organic cyanides such as acetonitrile and acrylonitrile. Cyanide is contained in cassava and bitter almonds in daily life, and hydrogen cyanide is also contained in car exhaust and cigarette smoke from human activities. 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 hyd...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/42G01N21/78G01N21/64
Inventor 徐骁董伟齐晓亮魏威刘玉成李军舰
Owner NANJING UNIV OF SCI & TECH
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