Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of fluorescent probe based on benzopyran nitrile derivatives and its preparation method and application

A benzopyran nitrile, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as free cyanide toxicity, achieve strong selectivity, wide potential application value, sensitivity high effect

Inactive Publication Date: 2021-02-02
HENAN POLYTECHNIC UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, free cyanide is highly toxic, and sodium / potassium cyanide is listed as a national first-class dangerous substance, which is strictly controlled by the public security department.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of fluorescent probe based on benzopyran nitrile derivatives and its preparation method and application
  • A kind of fluorescent probe based on benzopyran nitrile derivatives and its preparation method and application
  • A kind of fluorescent probe based on benzopyran nitrile derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of Benzopyranonitrile Derivatives

[0029]

[0030] Dissolve 0.624g of 2-(2-(4-hydroxystyryl)-4H-chroman-4-ethylidene)malononitrile and 1.265g of triethylamine in 40mL of dichloromethane, add dropwise under ice-cooling 0.588g thiophenoyl chloride, stirred at room temperature for 8h. The solvent was evaporated under reduced pressure, and the solid residue was recrystallized with a mixed solvent of dimethylformamide and water (1:1, volume ratio) to obtain the target product, and the yield of the target product was 56%.

[0031] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the benzopyranonitrile derivative that makes, the result is as follows:

[0032] 1 H NMR (400MHz, DMSO-d 6 )δ: 8.74-8.76(d, J=8.4Hz, 1H), 8.12-8.13(d, J=5.2Hz, 1H), 8.05-8.06(d, J=3.6Hz, 1H), 7.93-7.97(t , J=8.0Hz, 1H), 7.87-7.89(d, J=8.8Hz, 2H), 7.83(s, 1H), 7.79-7.81(d, J=8.8Hz, 1H), 7.62-7.66(t, J=8.0Hz, 1H), 7.55-7.59(d, J=16.0Hz, 1...

Embodiment 2

[0036] Determination of Optical Properties of Benzopyranonitrile Derivatives to Cyanide

[0037] The benzopyranonitrile derivatives prepared in the above example 1 were used as fluorescent probes in DMSO / H 2 O (volume ratio 9:1) medium to prepare a molar concentration of 1 × 10 -5 mol / L solution, respectively, at a molar concentration of 5×10 -4 mol / L of AcO - , Br - , Cl - , ClO - , CN - , F - , I - , PO 4 3- , PPi, HSO 3 - , S 2- , N 3 - and SCN - Add an equal amount of the above-mentioned fluorescent probe solution to the solution of the anion, and analyze it with a UV-visible spectrometer, and the resulting UV spectrogram is shown in Figure 4 . pass Figure 4 It can be seen that the benzopyranonitrile derivative prepared in Example 1 of the present invention as a fluorescent probe only has a significant response to cyanide, the color of the probe solution changes from light yellow to green, and other ions remain unchanged. pass Figure 5 The ultraviolet ...

Embodiment 3

[0040] Detection experiment of benzopyranonitrile derivative fluorescent probe in intracellular cyanide

[0041] 1 x 10 for HeLa cells -5 The benzopyranonitrile derivative fluorescent probe prepared in the above-mentioned embodiment 1 of M was incubated for 0.5 hours and then added CN - After continuing to incubate for 0.5 hours, use the Olympus FV500-IX70 laser confocal microscope to perform fluorescence imaging, and obtain the fluorescence imaging map of HeLa cells, specifically as follows Figure 7 As shown, wherein a is the fluorescence imaging image of the above-mentioned fluorescent probe; b is the imaging image of the above-mentioned fluorescent probe under bright field; c is the superimposed picture of the above-mentioned fluorescent probe bright-field image and fluorescence image; d is the image of the above-mentioned fluorescent probe +CN - Fluorescence imaging; e is the above fluorescent probe + CN - Imaging image under bright field; f is the above fluorescent pr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention provides a fluorescent probe based on a benzopyran nitrile derivative, a preparation method and application thereof, wherein the chemical structural formula of the benzopyran nitrile derivative is as follows: Under physiological conditions, it can selectively interact with cyanide, the color of the solution changes from light yellow to green, and the near-infrared fluorescence is significantly enhanced, especially as a fluorescent probe for the convenient detection of cyanide in cells.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a fluorescent probe based on benzopyranonitrile derivatives, a preparation method and application thereof. Background technique [0002] Cyanide is widely used in gold mining, electroplating, metallurgy, etc., and plays an important role in industrial production. However, free cyanide is highly toxic, and sodium / potassium cyanide is listed as a national first-class dangerous substance, which is strictly controlled by the public security department. Still, cyanide spills happen from time to time. Cyanide is easily absorbed by the human body and can enter the human body through the mouth, respiratory tract or skin. An overdose of cyanide can cause vomiting, convulsions, loss of will and eventually death. Therefore, the detection of cyanide is of great significance in the fields of life science and environmental detection. [0003] Fluorescent chemical sensors for th...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D409/12G01N21/64
CPCC07D409/12C09K11/06C09K2211/1007C09K2211/1088C09K2211/1092G01N21/643G01N21/6486
Inventor 王元吴伟娜王贝贝薛文招吕目轩
Owner HENAN POLYTECHNIC UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com