Synthesis and application of fluorescent probe for simultaneously distinguishing gold ions and palladium species

A technology of fluorescent probes and fluorescent molecular probes, applied in the synthesis and application of fluorescent probes that simultaneously distinguish between gold ions and palladium species

Active Publication Date: 2021-07-16
HUNAN NORMAL UNIVERSITY
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some have been reported for the detection of gold ions (Au 3+ ) or palladium species (Pd 0 , Pd 2+ , Pd 4+ ) fluorescent probes, but the current differential detection of gold ions (Au 3+ ) with palladium species (Pd 0 , Pd 2+ , Pd 4+ ) of bifunctional fluorescent probes have not been reported

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
  • Synthesis and application of fluorescent probe for simultaneously distinguishing gold ions and palladium species
  • Synthesis and application of fluorescent probe for simultaneously distinguishing gold ions and palladium species
  • Synthesis and application of fluorescent probe for simultaneously distinguishing gold ions and palladium species

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1. Synthesis of 5-ethyl-8-methoxy-1,2,3,3a,4,5-hexahydropyrrolo(1,2-a)quinoxaline

[0028] a. Add 30 g (175.31 mmol) 3-fluoro-4-nitroanisole and 37.5 g (227.9 mmol) L-proline methyl ester hydrochloride to 200 mL of anhydrous acetonitrile, then add 73 mL ( 525.9 mmol) triethylamine heating and reflux reaction for 6 hours, filtered to remove triethylamine hydrochloride, spin-dried solution,

[0029] b. Dissolve the spin-dried solution with 300 mL of methanol, slowly add 46.76 g (874.13 mmol) of ammonium chloride and 57.15 g (874.13 mmol) of zinc powder, stir overnight at room temperature, then filter to remove the zinc powder, spin to dry the solvent, The solid was added to water and filtered to obtain a green solid,

[0030] c. Dissolve the green solid in 400 mL of anhydrous tetrahydrofuran, add 36.4 g (962.17 mmol) of sodium borohydride and 122 mL (962.17 mmol) of boron trifluoride ether, and react at 90°C for 12 hours. After the reaction is complete, slowly po...

Embodiment 2

[0032] Example 2. Synthesis of 5-ethyl-8-hydroxyl-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxaline-7-carbaldehyde

[0033] . Under nitrogen protection, add 10 mL (64.22 mmol) of phosphorus oxychloride (POCl 3 ), stirred at 20-50°C for 30-60 minutes to obtain a yellow solution, and 10 g (35.68 mmol) of 5-ethyl-8-methoxy-1,2,3a,4,5-hexahydropyrrole And (1,2-a) quinoxaline was dissolved in 40mL N,N-dimethylformamide (DMF), and added dropwise to the yellow mixed solution, and the mixture continued to stir and react at 60°C under nitrogen protection for 12 hours; After the reaction was complete, the reaction solution was poured into an appropriate amount of ice water, and the pH was adjusted to 5-6 with 20% NaOH solution, then extracted with ethyl acetate, and the organic layer was spin-dried to obtain a yellow solution.

[0034] . Add 621.8 mg (23.05 mmol) of aluminum and 5.85 g (23.05 mmol) of iodine into 15 mL of anhydrous acetonitrile, react for 10 minutes, dissolve the a...

Embodiment 3

[0035] Example 3. Synthesis of 2-((5-ethyl-8-(prop-2-yn-1-yloxy)-1,2,3,3a,4,5-hexahydropyrrolo[1,2 -a]quinoxal-7-yl)methylene)malononitrile

[0036] . 200 mg (811.9μmol) 5-ethyl-8-hydroxyl-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxaline-7-carbaldehyde and 289 mg (2.44 mmol) acryloyl chloride was added to 8 mL of anhydrous dichloromethane, then 246.5 mg (2.44 mmol) redistilled triethylamine was added, reacted at room temperature for 3 hours, passed through the column to obtain 140 mg of a cyan solid, and the yield was 60.63%;

[0037] . Step 140 mg (492.3 μmol) of solid and 39.02 mg (590.80 μmol) of malononitrile were added to 8 mL of ethanol, reacted overnight at room temperature, and filtered to obtain the fluorescent molecular probe 2-((5-ethyl-8- (prop-2-yn-1-yloxy)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxal-7-yl)methylene)propanedi Nitrile 101mg, yield 61.72%.

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 bifunctional fluorescent probe for simultaneously distinguishing gold ions (Au < 3 + >) and palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >). The chemical structural formula of the molecular probe is shown in the description. The fluorescent probe can be subjected to different chemical reactions with gold ions (Au < 3 + >) and palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >) to generate products with different optical properties, the probe reacts with the gold ions (Au < 3 + >) to emit green light of 484 nm under the excitation wavelength of 422 nm, and reacts with the palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >) to emit red light of 606 nm under the excitation wavelength of 472 nm, so that the purpose of simultaneously distinguishing the gold ions (Au < 3 + >) and the palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >) in two channels is fulfilled. The fluorescent molecular probe disclosed by the invention can be used for quantification of gold ions (Au < 3 + >) and palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >) in the environment and simultaneous fluorescence imaging analysis of gold ions (Au < 3 + >) and palladium species (Pd<0>, Pd < 2 + > and Pd < 4 + >) in living cells, and has a huge application prospect in the technical fields of environment, life science and the like.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a gold ion (Au 3+ ) with palladium species (Pd 0 , Pd 2+ , Pd 4+ ) synthesis of fluorescent probes, and the quantitative detection of gold ions (Au 3+ ) with palladium species (Pd 0 , Pd 2+ , Pd 4+ ), simultaneously differentiated imaging gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ )Applications. Background technique [0002] Fluorescent probes have the characteristics of high sensitivity, visualization, easy operation, and low cost. In recent decades, various fluorescent probes have been widely used in the detection of various metal ions. The design and synthesis of multi-signal and multi-detection fluorescent molecular probes can be applied to the detection and quantification of various metal ions, and have high application value in the fields of analytical chemistry and environmental pollutant detection. In recent years, ...

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): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06G01N21/643C09K2211/1044Y02P10/20
Inventor 尹鹏陈洁甘亚兵尹国兴李海涛
Owner HUNAN NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap