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

Non-periphery substituted phthalocyanine metal complex and preparing method thereof

A metal complex, non-peripheral technology, applied in zinc organic compounds, organic chemistry, etc., can solve problems such as difficult aggregation, and achieve the effects of difficult aggregation, easy access to synthetic raw materials, and easy operation

Inactive Publication Date: 2010-10-13
FUZHOU UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a fluorescent probe used in the field of medicine, it also needs to have the characteristics of hydrophilicity, low aggregation, high stability and easy synthesis. However, there are still few reports on phthalocyanine complexes with high fluorescence quantum yields with the above characteristics.

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
  • Non-periphery substituted phthalocyanine metal complex and preparing method thereof
  • Non-periphery substituted phthalocyanine metal complex and preparing method thereof
  • Non-periphery substituted phthalocyanine metal complex and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0054] The steps of the preparation method of the non-peripheral four-substituted phthalocyanine metal complex of structural formula (1) are:

[0055] (1): With 3-nitrophthalonitrile and the alcohol derivative of the substituting group described in claim 1 as the reactant, the molar ratio of the two is 1: 0.8-1.2; the alcohol derivative is butylparaben, 4-hydroxybenzoic acid, 3-(4-hydroxyphenyl)propionic acid, 3-hydroxybenzoic acid, methyl salicylate, ethyl N-acetyltyrosine, or N-acetyl One of the base tyrosine;

[0056] (2): With dimethyl sulfoxide or N, N-dimethylformamide as solvent, the amount of solvent needs 3-8ml for every mmol reactant 3-nitrophthalonitrile, in the presence of potassium carbonate and nitrogen Under the protection of room temperature-60°C, react for 8-24 hours to obtain the intermediate substituted phthalonitrile, the substituted phthalonitrile is as shown in formula (3), R and the substituting group R described in claim 1 same;

[0057] (3): Using t...

Embodiment 1

[0083] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-butoxycarbonylphenoxy)phthalocyanine zinc(II)

[0084] This compound can also be called four-a-(4-butoxycarbonylphenoxy)zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:

[0085]

[0086] (1) Preparation of intermediate 3-(4-butoxycarbonylphenoxy) phthalonitrile:

[0087] Under the protection of nitrogen, 5mmol butylparaben and 4-6mmol (preferably 5mmol) 3-nitrophthalonitrile were added to 15-40ml (preferably 20ml) dimethyl sulfoxide (DMSO) or N, N - In dimethylformamide (DMF), after stirring at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, and react for 12 to 24 hours (preferably 16 hours). The reaction mixture was added to 200ml of ice-water mixture, stirred to precipitate a large amount of white precipitate, left to stand, filtered by suction, washed with water until neutral, the filter cake was collected, dried under normal pressure at 70°C to obt...

Embodiment 2

[0094] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-carboxyphenoxy)phthalocyanine zinc(II)

[0095] This compound can also be called four-a-(4-carboxyphenoxy) zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:

[0096]

[0097] (1) Preparation of intermediate 3-(4-carboxyphenoxy) phthalonitrile:

[0098] Under the protection of nitrogen, dissolve 0.69g (5mmol) 4-hydroxybenzoic acid, 0.87g (5mmol) 3-nitrophthalonitrile in 20ml dimethyl sulfoxide (DMSO), stir at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, after 10 minutes, add 1.0 g of potassium carbonate, and continue the reaction for 12 to 24 hours (preferably 14 hours). Suction filter the reaction mixture, collect the filtrate, add 200ml ice-water mixture to the filtrate, adjust the pH value to 1~3 (preferably 2) with 2mol / L HCl solution, the product is precipitated out, filter, wash with water until neutral, collect The filter cake was dried under ...

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

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention discloses several non-peripherial substituted phthalocyanine metal complexes and making method, which introduces functional group into position a (position 1(4), 8(11), 15(18) and 22(25)) of phthalocyanine complex.

Description

technical field [0001] The invention belongs to the field of organic functional materials (including medical materials), and specifically relates to a non-peripheral substituted phthalocyanine metal complex and a preparation method thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which have been widely used in textile, printing and many other high-tech fields. Phthalocyanine metal complexes are also used as photosensitizers in photodynamic therapy (or diagnosis or purification or disinfection), or as fluorescent probes in biosensors. [0003] However, the currently reported biologically active phthalocyanine complexes still have deficiencies, such as lack of water solubility, poor stability, or complex synthetic routes, which need further improvement. Most planar substituted phthalocyanine photosensitizers are highly aggregated in physiological systems, resulting in a significant decrease in their fluorescence q...

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): C07D497/22C07F3/06
Inventor 黄剑东柯美荣
Owner FUZHOU 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