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

Pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe as well as preparation method and application of pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe

A technology of arylene nitrile carbazoles and fluorescent probes, which is applied in the detection field and can solve problems such as poor hydrophilicity, low probe sensitivity, and small conjugated systems

Pending Publication Date: 2022-07-22
GUIZHOU UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the current research on fluoride ion fluorescent probes has made significant progress, most of the probes have low sensitivity and poor hydrophilicity, and are difficult to be used for the quantitative detection of fluoride ions in biological samples (cells, blood, urine) in aqueous phase systems.
Such as CN111039972A, the probe has poor water solubility and is only suitable for quantitative detection of fluoride ions in pure acetonitrile. The formation of Ar-OH after responding to fluoride ions is susceptible to interference, and its conjugated system is small and has low sensitivity, so it is not applicable Quantitative detection of trace fluoride ions

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
  • Pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe as well as preparation method and application of pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe
  • Pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe as well as preparation method and application of pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe
  • Pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe as well as preparation method and application of pyridine ring-containing aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A method for preparing a pyridine ring-containing aryl nitrile carbazole reactive fluoride ion fluorescent probe, comprising the following steps:

[0035] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0036] In a 100 mL round bottom flask, 2-methoxy-9H-carbazole (5.91 g, 30 mmol) and sodium hydroxide (6 g, 150 mmol) were added and dissolved in DMSO (60 mL), and iodopropane (10.2 mmol) was added with stirring. g, 60 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 60 °C for 16 h after vacuuming for three times. After the reaction was completed, it was cooled to room temperature, diluted with 60 mL of water, extracted with dichloromethane (60 mL×3), the organic phases were combined and washed with saturated NaCl solution (100 mL×2), then anhydrous sodium sulfate was added and allowed to stand for 15 min, and the mixture was rotated under reduced pressure....

Embodiment 2

[0046] A method for preparing a pyridine ring-containing aryl nitrile carbazole reactive fluoride ion fluorescent probe, comprising the following steps:

[0047] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0048] In a 100 mL round-bottomed flask, 2-methoxy-9H-carbazole (4.93 g, 25 mmol) and sodium hydroxide (5 g, 125 mmol) were added and dissolved in DMSO (50 mL), and iodopropane (10.6 mmol) was added with stirring. g, 62.5 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 60 °C for 16 h after vacuuming for three times. After the reaction was completed, cooled to room temperature and diluted with 50 mL of water, extracted with dichloromethane (50 mL×3), the organic phases were combined and washed with saturated NaCl solution (80 mL×2), then anhydrous sodium sulfate was added and allowed to stand for 15 min, and the mixture was rotated under reduced pressure. ...

Embodiment 3

[0058] A method for preparing a pyridine ring-containing aryl nitrile carbazole reactive fluoride ion fluorescent probe, comprising the following steps:

[0059] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0060] In a 100 mL round-bottom flask, 2-methoxy-9H-carbazole (5.91 g, 30 mmol) and potassium hydroxide (6.72 g, 120 mmol) were added and dissolved in DMSO (60 mL), and iodopropane ( 15.3 g, 90 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 65 °C for 14 h after vacuuming for three times. After the reaction was completed, it was cooled to room temperature, diluted with 60 mL of water, extracted with dichloromethane (60 mL×3), the organic phases were combined and washed with saturated NaCl solution (100 mL×2), then anhydrous sodium sulfate was added and left to stand for 15 min, and the mixture was rotated under reduced pressure. The crude product was obt...

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 relates to the technical field of detection, in particular to an aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe containing a pyridine ring as well as a preparation method and application of the aryl alkene nitrile carbazole reaction type fluorine ion fluorescent probe. According to the invention, carbazole is used as a fluorophore, a silicon-oxygen bond is used as a recognition group, a pyridine group is introduced through a Knoevenagel condensation reaction, and the compound 3-((2-((tert-butyldimethylsilyl) oxy)-9-propyl-9H-carbazole-3-yl) 2-(pyridine-2-yl) acrylonitrile is synthesized. The fluorine ions induce Si-O bond breakage through Lewis acid-base reaction to form O-attacking ortho-aryl allylazonitrile groups to perform cyclization, and the conjugate area of the probe is greatly increased, so that the quantum yield is greatly improved, and the fluorescence intensity is remarkably changed to realize the detection of the fluorine ions in a biological sample. The fluorescent probe is a ratio-type fluorescent probe which has the characteristics of wide range and high sensitivity in response to fluorine ions, and can realize quantitative detection of trace fluorine ions in a blood sample.

Description

technical field [0001] The invention relates to the technical field of detection, in particular to a pyridine ring-containing aralene nitrile carbazole reactive type fluoride ion fluorescent probe and a preparation method and application thereof. Background technique [0002] Fluoride ion is one of the essential trace elements for the human body. An appropriate amount of fluoride can strengthen bones and teeth, and can effectively prevent dental caries and treat human osteoporosis. Excessive fluoride ions will inhibit the synthesis of DNA and protein in the human body, lead to metabolic disorders of the immune system, and reduce human immunity. In addition, it will lead to a drop in blood pressure and affect human growth and development. Therefore, the determination of fluoride ion concentration in biological samples is of great significance for further understanding the pathological process of various diseases related to fluoride ion. [0003] Fluorine reagent colorimetry...

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): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/1892C09K11/06G01N21/643G01N21/6458C09K2211/1029
Inventor 刘力李丹乐意鄢龙家饶念
Owner GUIZHOU 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