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

A kind of pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and its preparation method

A fluorescent probe, Schiff base cobalt technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of detection effect interference, inability to perform quantitative detection, single detection mode, etc., and achieve good practical value. Effect

Active Publication Date: 2022-03-25
NANJING FORESTRY UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The detection effect of these fluorescent probes is not only susceptible to interference from external factors such as competing ions, reaction time, and pH range, but also has a single detection mode, which is sensitive to different concentrations of Co 2+ Quantitative detection is not possible

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 pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and its preparation method
  • A kind of pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and its preparation method
  • A kind of pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of camphorquinone 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-metamethylenepyridazino[4,5-b]quinoxaline-1,4- The reaction formula of diamine 2-hydroxy-1-naphthalenecarboxaldehyde bis-Schiff base is:

[0031]

[0032]

[0033] Specific steps are as follows:

[0034] 1) Preparation of 5,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methylenequinoline-2,3-dicarbonitrile:

[0035] 0.9 mmol of camphorquinone, 1 mmol of 2,3-diaminomaleonitrile and 7 mL of acetic acid were successively added to a dry three-necked flask, the reaction was refluxed for 4 h, followed and monitored by TLC, and the reaction was stopped after the reaction was complete; the reaction solution was decompressed After the acetic acid was distilled off, dichloromethane was added, washed with saturated brine until neutral, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to obtain 5,9,9-trimethyl-5,6,7 , 8-tetrahydro-5,8-methylenequinoline-2,3-dicarbonitrile cru...

Embodiment 2

[0041] 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methylenepyridazino[4,5-b]quinoxaline-1,4-diamine 2-Hydroxy-1-naphthaldehyde bis-Schiff base was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare 0.5×10 -5 M concentration probe solution, the CoCl 2 ·6H 2 O was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare solutions with concentrations of 0, 2.0, 4.0, 6.0, 8.0, 10.0, 12.0, 14.0, 16.0, 18.0, 20.0 μM. Different concentrations of cobalt ion pair 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methylenepyridazino were measured by standard titration under spectrofluorophotometer The fluorescence emission spectrum of [4,5-b]quinoxaline-1,4-diamine acetal 2-hydroxy-1-naphthaldehyde bis-Schiff base, as shown in figure 1 shown. The results showed that the orange-yellow fluorescence of the solution was quenched with the increasing concentration of cobalt ions in the system within the concentration range of 0-20 μM, which indicated that the probe could detect cobalt ions sensitively and qua...

Embodiment 3

[0043] 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methylenepyridazino[4,5-b]quinoxaline-1,4-diamine 2-Hydroxy-1-naphthaldehyde bis-Schiff base was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare 0.5×10 -5 M concentration of probe solution, various metal salt compounds were dissolved in PBS / THF (v / v=6 / 4) buffer to prepare 1.0×10 -4 M concentration of metal ion solution (Co 2+ , K + , Na + , Ca 2+ , Zn 2+ , Fe 3+ , Fe 2+ , Sn 2+ , Cr 2+ , Cs + , Ni 2+ , Ce 4+ , La 3+ , Al 3+ , Cu 2 + , Ag + , Mg 2+ , Mn 2+ , Hg 2+ , Pb 2+ , Cd 2+ ). Different ion pairs 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methylenepyridazino[4 , 5-b]quinoxaline-1,4-diamine acetal 2-hydroxy-1-naphthaldehyde bis-Schiff base fluorescence emission spectrum, such as figure 2 shown. The results show that the fluorescence is significantly quenched after the addition of cobalt ions to the probe solution, while the addition of other ions such as K + , Na + , Ca 2+ , Zn 2+ , Fe 3+ , Fe 2...

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 pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and a preparation method thereof. The present invention utilizes camphor derivative camphorquinone as a raw material, and carries out cyclization reaction with 2,3-diaminomaleonitrile to obtain 5,9,9-trimethyl-5,6,7,8-tetrahydro-5, 8-bridge methylene quinoline-2,3-dicarbonitrile; then carry out condensation cyclization reaction with hydrazine hydrate to obtain 6,11,11-trimethyl-6,7,8,9-tetrahydro-6 , 9-bridge methylene pyridazino[4,5-b]quinoxaline-1,4-diamine; and then carry out condensation reaction with 2-hydroxyl-1-naphthaldehyde to obtain 6,11,11-three Methyl-6,7,8,9-tetrahydro-6,9-methanopyridazino[4,5-b]quinoxaline-1,4-diamine condensed 2-hydroxy-1-naphthalene Formaldehyde bis-Schiff base. The compound can rapidly and exclusively bind Co at room temperature 2+ Complexation occurs, so that the orange-yellow fluorescence of the solution is quenched, and the color of the solution changes from orange-red to dark red under sunlight. It can be used as a fluorescent probe for detecting cobalt ions, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a pyridazinoquinoxalinediamine Schiff base cobalt ion fluorescent probe and a preparation method thereof. Background technique [0002] Cobalt is an essential trace element for the human body. Its physiological functions mainly involve the composition of vitamin B12, which is necessary for the formation of red blood cells. Cobalt deficiency can lead to pernicious anemia, but excessive intake can lead to polycythemia or excess red blood cells and heart disease. Long-term inhalation of dust or fumes can affect lung function and can cause lung diseases such as diffuse nodular fibrosis. Cobalt may cause memory deficits in humans and has been reported to cause neurotoxicity in animal models. Skin contact can cause allergic skin reactions, resulting in allergic dermatitis. According to reports, Co 2+ The ions are genotoxic in vitro and in vivo and are carcinogenic. I...

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): C07D487/08C09K11/06G01N21/64
CPCC07D487/08C09K11/06G01N21/6428C09K2211/1074G01N2021/6432
Inventor 王石发刘豪闯杨海燕王忠龙李明新张燕杨益琴徐徐
Owner NANJING FORESTRY 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