A preparation method and application of a ratiometric near-infrared fluorescent probe for detecting cyanide

A fluorescent probe and cyanide technology, which is applied in the field of fluorescence detection, can solve the problems of fluorescent signal artifacts and the reduction of detection accuracy of fluorescence analysis, and achieve the effects of reducing difficult-to-separate impurities, preventing side reactions and improving accuracy.

Active Publication Date: 2021-08-03
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, when fluorescent probes are used to analyze and detect cyanide in food samples, factors such as the distribution of the probe in the food, the photobleaching of the probe, and the efficiency of the instrument often cause false fluorescence signals during the analysis and detection, which also lead to the detection of cyanide in the fluorescence analysis. Reduced accuracy

Method used

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  • A preparation method and application of a ratiometric near-infrared fluorescent probe for detecting cyanide
  • A preparation method and application of a ratiometric near-infrared fluorescent probe for detecting cyanide
  • A preparation method and application of a ratiometric near-infrared fluorescent probe for detecting cyanide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Add 3g of 4-(diethylamino) salicylaldehyde in a 150mL flask, dissolve it with 20mL of absolute ethanol, then add 4.7mL of diethyl malonate, stir well, then add 0.83mL of piperidine to obtain For mixed solution A, heat the mixed solution at 90°C to reflux and stir for 7 hours; after the reaction, cool to room temperature, use a rotary evaporator to remove excess solvent, and add 20 mL of the same amount of acetic acid and hydrochloric acid sequentially under ice-water bath conditions, followed by 100 The reaction was carried out under reflux at ℃ for 12 hours; after the reaction was completed, the pH was adjusted to 5 with sodium hydroxide solution in an ice-water bath, and the precipitate was filtered under reduced pressure to obtain a filter cake, which was then recrystallized with absolute ethanol at 90°C and dried in vacuo. Obtain 7-(diethylamino)coumarin as a khaki solid;

[0043] (2) First prepare the Wells reagent with 5mL of phosphorus oxychloride and an equa...

Embodiment 2

[0047] (1) Add 4g of 4-(diethylamino) salicylaldehyde to a 150mL flask, dissolve it in 25mL of absolute ethanol, then add 4mL of diethyl malonate, stir well, then add 0.5mL of piperidine to obtain a mixture Solution A: Heat the mixed solution at 90°C to reflux and stir for 7 hours; after the reaction, cool to room temperature, use a rotary evaporator to remove excess solvent, add 15mL of the same amount of acetic acid and hydrochloric acid successively under the condition of an ice-water bath, and then reflux at 105°C Heat to reflux for reaction for 12 hours; after the reaction, adjust the pH to 5 with sodium hydroxide solution in an ice-water bath, filter the precipitate under reduced pressure to obtain a filter cake, recrystallize with absolute ethanol at 90°C, and dry in vacuo to obtain 7-(diethylamino)coumarin khaki solid;

[0048] (2) First prepare the Wells reagent with 5mL of phosphorus oxychloride and an equal volume of DMF, then use 3.5mL of DMF to completely dissolve...

Embodiment 3

[0052] (1) Add 3g of 4-(diethylamino) salicylaldehyde to a 150mL flask, dissolve it with 30mL of absolute ethanol, then add 6mL of diethyl malonate, stir well, then add 1mL of piperidine to obtain a mixed solution A. Heat the mixture at 95°C to reflux and stir for 6 hours; after the reaction, cool to room temperature, use a rotary evaporator to remove excess solvent, add 10mL of acetic acid and hydrochloric acid in the same amount in an ice-water bath, and then heat at 100°C The reaction was carried out under reflux for 13 hours; after the reaction was completed, the pH was adjusted to 5 with sodium hydroxide solution in an ice-water bath, and the precipitate was filtered under reduced pressure to obtain a filter cake, which was then recrystallized with absolute ethanol at 90°C and dried in vacuo to obtain 7 -(diethylamino)coumarin khaki solid;

[0053] (2) First prepare the Wells reagent with 5mL of phosphorus oxychloride and an equal volume of DMF, then completely dissolve t...

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Abstract

The invention relates to the technical field of fluorescence detection, in particular to a preparation method and application of a ratio-type near-infrared fluorescent probe for detecting cyanide in food; the preparation steps are as follows: firstly prepare and obtain 7-(diethylamino)coumarin and 7‑(diethylamino)coumarin aldehyde; then 7‑(diethylamino)coumarin aldehyde and (1,3‑dioxychloro‑2‑methyl)triphenylphosphine bromide were added to Dissolve in dichloromethane, add dropwise sodium hydroxide solution, add hydrochloric acid to neutralize, obtain the intermediate product through extraction and separation, and column chromatography purification; add the intermediate product and acetophenone to the mixed solvent of dichloromethane and methanol, and then Add tetrahydropyrrole dropwise, add sodium chloride, stir, distill, and column chromatography purify to obtain the ratio-type near-infrared fluorescent probe for detecting cyanide; the present invention has developed a novel high-performance ratio-type near-infrared fluorescent probe , the synthesis method is simple, has good selectivity to cyanide, and has been successfully applied to the detection of cyanide in food.

Description

technical field [0001] The invention relates to the technical field of fluorescence detection, in particular to a preparation method and application of a ratio-type near-infrared fluorescent probe for detecting cyanide. Background technique [0002] It is well known that cyanide (CN - ) is a toxic agent that can cause death in very small doses. In living organisms, cyanide binds tightly to cytochrome oxidase, thereby inhibiting cellular respiration. Although cyanide is very toxic, it is still widely used in various industrial production processes, such as metallurgy, gold mining, electroplating, plastic manufacturing, etc. When the industrial waste liquid is not handled properly, the cyanide in the industrial waste liquid may contaminate food and water sources, thus posing a threat to human food safety. In addition, cyanogenic glycosides are widely distributed in thousands of plants, including sorghum, almonds, flax, bamboo shoots, cherry kernels, potatoes, cassava and ot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
Inventor 龙凌亮韩园园曹思雨袁湘琦刘卫国陈倩
Owner JIANGSU UNIV
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