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Zinc phthalocyanine complex and preparation method thereof

A technology of zinc phthalocyanine and complexes, which is applied in the field of organic and metal coordination compound synthesis, can solve the problems of many side reactions, difficult synthesis, difficult separation, etc., and achieves the advantages of less side reactions, easily available raw materials, and simple synthesis method. Effect

Inactive Publication Date: 2012-10-03
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing substituted phthalocyanine metal complexes have problems such as difficult synthesis, many side reactions, and difficult separation.

Method used

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  • Zinc phthalocyanine complex and preparation method thereof
  • Zinc phthalocyanine complex and preparation method thereof
  • Zinc phthalocyanine complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] 1) Synthesis of 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate: 32.00g (0.30mol) triethylamine, 24.00g (0.16mol) triethylene glycol and 7.60g (0.04mol) p-toluenesulfonate Benzenesulfonyl chloride was reacted in dichloromethane (70ml) system at 25°C for 10 hours. After the reaction was completed, it was extracted with 200ml of 1M hydrochloric acid solution, saturated saline, and distilled water. The crude product was separated by silica gel column chromatography using petroleum ether-ethyl acetate (1:1, v / v) as the eluent to obtain 5.48 g (0.018 mol) of the product with a yield of 45%.

[0075] 2) Synthesis of 8-(7-coumarinyloxy)-3,6-dioxa-1-octanol: 2.76g (20mmol) anhydrous potassium carbonate, 1.52g (5mmol) 8-hydroxy-3,6 -Dioxa-octyl p-toluenesulfonate and 0.81 g (5 mmol) 7-hydroxycoumarin were reacted in N,N-dimethylformamide (DMF, 15ml) at 60°C for 8 hours, and the reaction After the end, the solvent was evaporated, and the crude product was extracted with dichlorome...

Embodiment 2

[0079] The preparation method is the same as Example 1. In the process of (1), the molar ratio of triethylamine, triethylene glycol and p-toluenesulfonyl chloride is 1:1:1, and react at 0°C for 12 hours in a dichloromethane system , other operations were the same, and the yield of 8-hydroxyl-3,6-dioxahoctyl p-toluenesulfonate was 38%. In the process of (2), the molar ratio of anhydrous potassium carbonate, 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate and 7-hydroxycoumarin is 3:1:1.2, in DMF at The reaction was carried out at 25°C for 12 hours. After the reaction was completed, the solvent was evaporated, and the crude product was extracted with chloroform, followed by methanol-chloroform as the eluent, and separated by silica gel column chromatography. The yield was 87%. In the process of (3), the molar ratio of anhydrous potassium carbonate, 8-(7-coumarinoxy)-3,6-dioxa-1-octanol and 3 or 4-nitrophthalonitrile The ratio is 5:1:1.2, reacted in DMF at 60°C for 12 hours, other o...

Embodiment 3

[0081] The preparation method is the same as Example 1. In the process of (1), the molar ratio of triethylamine, triethylene glycol and p-toluenesulfonyl chloride is 2:2:1, and react at 0°C for 12 hours in a dichloromethane system , other operations were the same, and the yield of 8-hydroxyl-3,6-dioxahoctyl p-toluenesulfonate was 41%. In the process of (2), the molar ratio of anhydrous potassium carbonate, 8-hydroxy-3,6-dioxahoctyl p-toluenesulfonate and 7-hydroxycoumarin is 3:1:1.5, in DMF at Reacted at 60°C for 24 hours. After the reaction, the solvent was evaporated, and the crude product was extracted with chloroform, followed by methanol-chloroform as eluent, and separated by silica gel column chromatography. The yield was 62%. In the process of (3), the molar ratio of anhydrous potassium carbonate, 8-(7-coumarinoxy)-3,6-dioxa-1-octanol and 3 or 4-nitrophthalonitrile The ratio is 4:1:1.5, reacted in DMF at 60°C for 12 hours, other operations are the same as in Example 1....

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Abstract

The invention relates to a zinc phthalocyanine complex and a preparation method thereof. The complex is (8-(7-coumarin oxygroup)-3,6-dioxoa-1-octyloxy; and the molecular formula of the zinc phthalocyanine complex is C42H32N8O6Zn. Coumarin oxygroup with a long alcoxyl chain is introduced at the periphery of the large ring of the zinc phthalocyanine, amphipathicity and biocompatibility of the zinc phthalocyanine complex are improved, and a photodynamic activity is improved. The zinc phthalocyanine complex is difficult to gather and favorable for improving cell intaking rate, and the photodynamic activity is improved; coumarin has an antitumor activity, and the coumarin is combined with photodynamic, so that the zinc phthalocyanine complex is favorable for serving as a photodynamic clinical medicine. The structure of a compound of the zinc phthalocyanine complex is single, and the compound is free from isomers, so that a product is easy to extract; and a synthetic method is simple, the side reaction is small, the yield is high, raw materials are readily available, cost is low, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, in particular to a zinc phthalocyanine complex and a preparation method thereof. Background technique [0002] Phthalocyanine is a class of macrocyclic compounds with good photophysical and photochemical properties. It is used in high-tech fields, including semiconductor devices, photovoltaics and solar cells, electrophotography, rectifiers, LB films, low-dimensional conductor materials, gas sensors, Electrocatalysis, deodorants, bactericides, photosensitizers for photodynamic therapy, etc., among which photosensitizers have great development prospects. [0003] The diversity and structural "tailoring" of phthalocyanine compounds provide the possibility for people to rationally design the required phthalocyanine compounds. Linking phthalocyanine with other functional groups to form new functional materials with complementary functions is one of the important ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K31/409A61P35/00
Inventor 薛金萍李俊
Owner FUZHOU UNIV
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