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Fluorescence chemical sensor and preparation method and application thereof

A chemical sensor and fluorescence technology, applied in the field of chemical sensors, can solve the problems of reduced sensitivity, reduced host-guest interaction, unable to effectively detect cyanide ions, etc., to achieve simple detection and improve application prospects.

Inactive Publication Date: 2011-09-21
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the cyanide ion fluorescent chemical sensor based on the host-guest interaction, because the strong solvation in aqueous solution reduces the interaction between the host-guest and greatly reduces the sensitivity, so this type of sensor cannot effectively detect cyanide ion in aqueous solution

Method used

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  • Fluorescence chemical sensor and preparation method and application thereof
  • Fluorescence chemical sensor and preparation method and application thereof
  • Fluorescence chemical sensor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, preparation of fluorescent chemical sensor (structural formula shown in formula (IV))

[0033]

[0034] (1) Weigh 180 mg of chloromethylpyridine hydrochloride and 700 mg of aniline into a reaction flask, use sodium hydroxide solution as a solvent, add hexadecyl ammonium bromide as a phase transfer catalyst, heat to 45 ° C and stir for 48 hours, Extracted with dichloromethane and separated by column chromatography (ethyl acetate / petroleum ether=3:1) to obtain pure pale yellow 4'-(N,N-dimethylpyridylamino)benzene. Slowly add 1ml of phosphorus oxychloride dropwise to anhydrous DMF sealed reaction bottle in ice bath, stir at 0°C for 30 minutes, then add 500mg of 4'-(N,N-dimethylpyridylamino) prepared above Benzene, heated to 45°C and stirred for 72 hours. After the reaction, the system was naturally cooled to room temperature, added distilled water and stirred for 30 minutes, adjusted the pH value to 10 with potassium carbonate, stirred for 30 minutes, ext...

Embodiment 2

[0046] Embodiment 2, preparation of fluorescent chemical sensor (structural formula shown in formula (VI))

[0047]

[0048] (1) The preparation method of 4'-(N,N-dimethylpyridylamino)benzaldehyde is the same as that in Example 1, wherein the temperature of the oxidation reaction is 90°C, and the time of the oxidation reaction is 24 hours.

[0049] (2) Weigh 300mg 2-methylbenzothiazole and 300mg methyl iodide into the reaction flask, use chloroform as a solvent, heat to 80°C and stir for 48 hours, a precipitate is formed, after the reaction stops, naturally cool to room temperature, filter Washing obtains light yellow 2-methyl-N-methylbenzothiazole iodide salt (its structural formula is shown in formula (III), wherein, R 1 for S, R 2 is methyl);

[0050] (3) Weigh 150mg 2-methyl-N-methylbenzothiazole iodine salt and 500mg 4'-(N,N-dimethylpyridylamino)benzaldehyde (wherein, 2-methyl-N- The molar ratio of methylbenzothiazole iodide salt and 4'-(N,N-dimethylpyridylamino)ben...

Embodiment 3

[0053] Embodiment 3, preparation of fluorescent chemical sensor (structural formula shown in formula (VIII))

[0054]

[0055] (1) The preparation method of 4'-(N,N-dimethylpyridylamino)benzaldehyde is the same as in Example 1, wherein the temperature of the oxidation reaction is 65°C, and the time of the oxidation reaction is 48 hours.

[0056] (2) 2-Methyl-N-methylbenzothiazole iodine salt The method is the same as that in Example 2.

[0057] (3) The preparation method of trans 2-[4'-(N,N-dimethylpyridylamino)styrene]-N-ylmethylbenzothiazole iodonium salt is the same as in Example 2.

[0058] (4) Weigh the corresponding sodium tetrafluoroborate corresponding to 20 times the equivalent of the product in (3), heat and reflux in water and ethanol solution for 24 hours to obtain the compound shown in formula (IX).

[0059]

[0060] (5) 54 mg of the compound represented by the formula (VI) was reacted with 18.8 mg of copper nitrate in water to obtain the fluorescent chemic...

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Abstract

The invention provides a fluorescence chemical sensor and a preparation method and application thereof. The structural formula of the fluorescence chemical sensor is shown as the formula (I), wherein R1 refers to sulfur or oxygen; and R2 refers to sulphonate, iodate, fluorphosphate or fluoborate. The preparation method for the fluorescence chemical sensor comprises the following steps of: (1) performing oxidation reaction on 4'-(N,N-dimethyl pyridyl amido)benzene under the action of an oxidant to obtain 4'-(N,N-dimethyl pyridyl amido)benzaldehyde; (2) reacting the 4'-(N,N-dimethyl pyridyl amido)benzaldehyde with a compound in a formula (III) to obtain a compound in a formula (II); and (3) reacting the compound in the formula (II) with copper ion-containing inorganic salt to obtain the fluorescence chemical sensor, wherein in the formulas (II) and (III), R1 refers to sulfur or oxygen; and R2 refers to sulphonate, iodate, fluorphosphate or fluoborate. The fluorescence chemical sensor can specifically, efficiently, timely and easily detect cyanide ions in aqueous solution.

Description

technical field [0001] The invention relates to a fluorescent chemical sensor and its preparation method and application, belonging to the technical field of chemical sensors. Background technique [0002] Cyanide salts are widely used in industry, including metallurgy, electroplating, dyes, medicine, etc. However, cyanide ion has strong toxicity. The national "Industrial Enterprise Design Hygienic Standard" stipulates that the maximum allowable concentration of cyanide ion in ground water is 0.05mg / L. Therefore, it is particularly important to detect cyanide ion in time and effectively. In recent years, many molecular devices for the chemical detection of cyanide ions, especially fluorescent chemical sensors for the detection of cyanide ions, have been reported successively, but the reports of fluorescent sensors for highly sensitive and selective detection of cyanide ions in aqueous phase are still relatively rare. [0003] Fluorescent chemical sensor is an analytical me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08C09K11/06G01N21/76
Inventor 陈玉哲杨清正陈红海李仲谨徐江飞吴骊珠
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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