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Non-periphery substituted phthalocyanine metal complex and preparing method thereof

A metal complex, non-peripheral technology, applied in the direction of zinc organic compounds, organic chemistry, etc., can solve the problem of not easy to aggregate, and achieve the effect of not easy to aggregate, easy to industrialize, and high stability

Inactive Publication Date: 2007-08-08
FUZHOU UNIV
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  • 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

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  • 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

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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 , react for 8-24 hours under room temperature-60 waste, obtain intermediate substituted phthalonitrile, described substituted phthalonitrile is as shown in formula (3), R and claim 1 described substituting group R same;

[0057] (3): Usi...

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 3-(4-carboxyphenoxy) phthalonitrile:

[0098] Under the protection of nitrogen, 0.69g (5mmol) 4-hydroxybenzoic acid, 0.87g (5mmol) 3-nitrophthalonitrile were dissolved in 20ml dimethyl sulfoxide (DMSO), after stirring 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 und...

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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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D497/22C07F3/06
Inventor 黄剑东柯美荣
Owner FUZHOU UNIV
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