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

Organic compounds used for detecting metal ion contents in solutions and applications thereof

A technology of organic compounds and metal ions, applied in organic chemistry, measuring devices, and analysis through chemical reactions of materials, etc., can solve problems such as high detection limit, inability to apply, and inability to make reversible sensors

Active Publication Date: 2015-08-12
FORLIGHTS DETECTION TECH LLC SUZHOU
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the selectivity of this series of fluorescent probes to calcium ions is extremely poor, and the response is only one hundredth of that of calcium ions. It is not suitable for the detection of magnesium ion concentration under the coexistence of calcium ions, but only suitable for the detection of magnesium ions in cells.
There are very few reports on the detection of magnesium ion concentration under the coexistence of calcium ions. Until recently, there have been some reports on the detection method of magnesium ions with fluorescent probes. Fluorescent probes that can be used for extracellular ion detection, but their detection limits are too high , is not sensitive to low concentration of magnesium, and the molecule does not contain functional groups that can be used for immobilization, so it cannot be used to make reversible sensors, so it cannot be applied to various samples that need to be used repeatedly, and the continuous detection of magnesium ions in blood or seawater detection

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
  • Organic compounds used for detecting metal ion contents in solutions and applications thereof
  • Organic compounds used for detecting metal ion contents in solutions and applications thereof
  • Organic compounds used for detecting metal ion contents in solutions and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1: the synthesis that contains amino ion complexing group

[0085] Synthesis of compound 3

[0086] Weigh compound 1 (1.00g, 5.99mmol, 1eq) into a 100mL three-neck flask, add 1,4-dioxane (30mL), replace the air in the flask with argon for 3 times, then add compound 2 (1.38g, 5.99mmol, 1eq), K 2 CO 3 (2.48g, 17.79mmol, 3eq), Pd(dppf)Cl 2 (244.61mg, 0.3mmol, 0.05eq), the air in the flask was replaced with argon again 3 times, the temperature was raised to 80°C, and the reaction was carried out overnight for 16h; thin layer chromatography TLC (PE:EA=3:1) showed that the reaction was complete; , the reaction solution was poured into 100mL water, extracted with 2×100mL EA, the combined EA phases were washed three times with an equal amount of water, separated, the EA phases were dried with anhydrous sodium sulfate, and concentrated to obtain the product compound 3 (1.60g, 95 %), without purification, continue to vote for the next step. 1H NMR (CDCl3) δ = 1.40...

Embodiment 2

[0093] Embodiment 2: the synthesis of the fluorescent indicator containing primary amino ion complexing group

[0094] Synthesis of compound 7

[0095]Compound 6 (20.00g, 61.28mmol) was weighed and dissolved in dimethylformamide (DMF, 100mL) in a 250mL three-neck flask, lithium chloride (7.79g, 183.85mmol) was added, and the temperature was raised to 110°C for overnight reaction. The progress of the reaction was detected by TLC (PE:EA=3:1), and the reaction reached equilibrium. Concentrate the reaction solution, add ethyl acetate to dissolve the soluble matter, filter, spin the filtrate to obtain 30 g of crude product, remove the oily substance by column chromatography, and recrystallize with petroleum ether: ethyl acetate: dichloromethane = 300ml: 100ml: 200ml to obtain the product 2.3 g (13%). 1H NMR (CDCl3) δ=1.29(s, 9H), 2.80(t, 2H), 3.25(t, 2H), 3.60(s, 3H), 6.80(s, 1H), 7.55(s, 1H).

[0096] Synthesis of Compound 8

[0097] Weigh compound 7 (2.3g, 7.36mmol) and disso...

Embodiment 3

[0116] Embodiment 3: the synthesis of the fluorescent indicator containing tertiary amino ion complexing group

[0117] Synthesis of Compound 21

[0118] Compound 13 (440mg, 0.1mmol) was weighed and dissolved in dichloromethane (20mL) in a 100mL single-necked bottle, trifluoroacetic acid (20mL) was added, and reacted at 30°C for 2 hours. After the completion of the reaction was detected by TLC (PE:EA=3:1), the organic phase was spin-dried to obtain 500 mg of the product, which was directly used in the next step.

[0119] Synthesis of compound 22

[0120] Weigh compound 21 (340mg) and DIEA (2ml, 19.03mmol) and dissolve it in NMP (4mL) in a reaction tube, add tert-butyl 4-chloro-1,8-naphthalene anhydride methylbenzoate (0.51g, 1.2eq ), react at 95 degrees for 24 hours. After TLC (DCM:MeOH=25:1) detected that the reaction was complete, pour the reaction solution into 200 mL of water, filter, dissolve the filter cake with dichloromethane, wash the organic phase with water three...

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 organic compounds used for detecting metal ion contents in solutions. The organic compounds can be used for biomedicine, environment monitoring, and the like. By introduction of color developing groups or fluorophores into ortho positions or the para position of 2-substituted phenyl of 2-(2'-substituted phenyl)-pyridine-6-carboxylic acid, and by utilization of the intramolecular charge transfer (ICT) principle or the photoinduced electron transfer (PET) principle, color developing or fluorescence intensity changes with changes of ion contents in solutions, so that contents of the metal ions in the solutions can be calculated according to ultraviolet absorption values or the fluorescence intensity. The organic compounds can be fixed onto surfaces of polymers and prepared into reversible metal ion sensors that can be used for a plurality of times, thus achieving real-time monitoring of contents of trace metal ions, making the whole analysis process automatic and largely increasing the efficiency.

Description

technical field [0001] The invention relates to the field of compounds used for detecting the content of metal ions in a solution, in particular to an organic compound used for detecting the content of metal ions in a solution and an application thereof. Background technique [0002] With global warming, the concentration of carbon dioxide in the air increases, and the alkalinity of seawater continues to weaken, which has a huge impact on the marine environment. The most influential parameter is the concentration of divalent cations in the water, mainly including magnesium and calcium. Magnesium ions are the most abundant divalent cations in organisms and in the environment. The fluctuation of magnesium ion concentration directly affects the survival and growth of aquatic animals and plants. The concentration of calcium ions in water depends on the concentration of magnesium ions. [0003] Traditional detection methods such as EDTA complexometric titration are very cumbers...

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): C07D401/12C07D401/14G01N21/78G01N21/64
CPCC07D401/12C07D401/14G01N21/643G01N21/78
Inventor 何华瑞
Owner FORLIGHTS DETECTION TECH LLC SUZHOU
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