Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fluorescent probe for detecting nitrite ions as well as preparation method and use method thereof

A technology of nitrite ion and fluorescent probe is applied in the field of coumarin derivatives and their preparation, which can solve the problems of quantitative detection of difficult nitrite ion samples, low detection sensitivity and high detection limit, and achieves easy popularization and high detection limit. The effect of application, sensitive and specific detection

Active Publication Date: 2019-11-22
ZHEJIANG SCI-TECH UNIV
View PDF3 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, currently reported probes are mainly fluorescent "on-off" type probes (see Adarsh, N.; Shanmugasundaram, M.; Ramaiah, D. Anal. Chem., 2013, 85, 10008-10012; Kumar, V.; Banerjee, M.; Chatterjee, A. Talanta, 2012, 99, 610-615; Chatterjee, A.; Khandare, D.G.; Saini, P.; ,2015,5,31479-31484), its detection sensitivity is low, which is not conducive to its detection in complex aqueous systems or in vivo
In addition, the detection limit of the current nitrite ion fluorescent probe is relatively high, it is difficult to quantitatively detect trace or even extremely trace nitrite ion samples

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
  • Fluorescent probe for detecting nitrite ions as well as preparation method and use method thereof
  • Fluorescent probe for detecting nitrite ions as well as preparation method and use method thereof
  • Fluorescent probe for detecting nitrite ions as well as preparation method and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the synthesis of compound PN1

[0039] Synthesis of 4-(2-nitrophenyl)-7-(dimethylamino)-2H-pyran-2-one (3)

[0040] With 6g 4-chloro-7-dimethylaminocoumarin (1) (26.2mmol) and 8g 2-nitrophenylboronic acid pinacol ester (2) (32.2mmol), 2g [1,1'-bis( Diphenylphosphino)ferrocene]palladium dichloride (2.9mmol) and 11g of potassium carbonate (80.5mmol) were dissolved in 400mL of 1,4-dioxane, and stirred at reflux for 12 hours. The reaction solution was suction filtered through diatomaceous earth, the filtrate was spin-dried, added 500mL of water, extracted with 500mL of ethyl acetate, and after concentration, the solid was recrystallized with 50mL of ethanol to obtain compound 4-(2-nitrophenyl)-7-(di Methylamino)-2H-pyran-2-one (3), this compound can be directly used in the next reaction.

[0041] Synthesis of 4-(2-aminophenyl)-7-(dimethylamino)-2H-pyran-2-one (4)

[0042] Dissolve 1 g of 4-(2-nitrophenyl)-7-(dimethylamino)-2H-pyran-2-one (3) (3.2 mmol) and ...

Embodiment 2

[0044] Embodiment 2, the color response of compound PN1 to nitrite ion

[0045] A test mother solution of dimethyl sulfoxide (DMSO) of the fluorescent probe PN1 for detecting nitrite ions of the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to a phosphate buffer with a certain concentration of nitrite ions, and use the corresponding phosphate buffer to make up to 10 mL, so that the concentration of the probe in the test solution is 1.0 μM, and the concentration of nitrite is 1.0 μM. Color response tests were performed at an ion concentration of 10.0 μM. Such as figure 2 and 3 As shown, after adding the nitrite ion aqueous solution, the color of the solution was observed from colorless to purple, and the fluorescence of the solution was also changed from red fluorescence to bright green fluorescence, indicating that the probe PN1 has an intuitive effect on nitrite ions. Color response.

Embodiment 3

[0046] Embodiment 3, the ultraviolet titration detection of different concentrations of nitrite ion to compound PN1

[0047] A test mother solution of dimethyl sulfoxide (DMSO) of the fluorescent probe PN1 for detecting nitrite ions of the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to phosphate buffer with different concentrations of nitrite ions, and use the corresponding phosphate buffer to adjust the volume to 10 mL, so that the concentration of the probe in the test solution is 1.0 μM, and the concentration of nitrite is 1.0 μM. The root ion concentration is 0-10.0μM for absorption spectrum test. The ultraviolet absorption curves in each system were obtained, and the standard curves of absorbance and nitrite ion concentration were established. Such as Figure 4 As shown, with the increase of nitrite ion concentration, the absorbance at 554nm increases gradually, while the absorbance at 55...

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 invention discloses a fluorescent probe for detecting nitrite ions as well as a preparation method and a use method of the fluorescent probe. A diazotization reaction of generating a diazonium salt from aniline and nitrite under an acidic condition is utilized to connect an aniline structure to the No.4 site of coumarin. The probe itself emits green fluorescence, but under the condition that nitrite ions exist, the aniline and nitrite generate the diazonium salt, then an intramolecular electrophilic substitution reaction occurs at the No.3 site of the coumarin, a long-wavelength fluorescence product is generated, and probe molecules emit strong red fluorescence. The coumarin dye-based ratio type nitrite probe provided by the invention has good response to a nitrite solution, can realize sensitive quantitative detection of trace nitrite in a sample, and has the advantages of simplicity and convenience in operation, low cost, sensitive response, easiness in popularization and application and the like.

Description

technical field [0001] The invention belongs to the field of organic small molecule fluorescent probes, and in particular relates to a coumarin derivative used as a nitrite ion fluorescent probe, a preparation method and a use method thereof. Background technique [0002] Nitrite ion (NO 2 - ) is widely used as a food preservative. Excessive nitrite can react with amino acids to produce strong carcinogen nitrosamines, which can cause various tumors including gastric cancer and intestinal cancer. In addition, excessive nitrite can also combine with hemoglobin in the blood, increasing the content of methemoglobin, resulting in tissue hypoxia, leading to various disease symptoms. Therefore, detecting the content of nitrite ions in food and drinking water is of great significance for ensuring the food safety of residents. [0003] Due to its excellent detection sensitivity and selectivity, and the ability to realize real-time and on-line detection of biological samples, fluor...

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
IPC IPC(8): C07D311/16C09K9/02C09K11/06G01N21/64
CPCC07D311/16C09K9/02C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N2021/6417G01N2021/6443
Inventor 韩益丰包诚丁钰章世深
Owner ZHEJIANG SCI-TECH UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com