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Alpha-(8-quinolineoxy)mono-substituted zinc phthalocyanine and preparation method thereof

A technology of quinolineoxyl and zinc phthalocyanine, applied in zinc organic compounds, organic chemistry, etc., can solve the problems of many side reactions, difficult separation, difficult synthesis, etc., achieve less side reactions, easy to obtain raw materials, and comprehensive synthesis method simple effect

Active Publication Date: 2008-09-10
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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  • Alpha-(8-quinolineoxy)mono-substituted zinc phthalocyanine and preparation method thereof
  • Alpha-(8-quinolineoxy)mono-substituted zinc phthalocyanine and preparation method thereof
  • Alpha-(8-quinolineoxy)mono-substituted zinc phthalocyanine and preparation method thereof

Examples

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Effect test

preparation example Construction

[0012] The steps of the preparation method are:

[0013] (1) Synthesis of 3-(8-quinolineoxy) phthalonitrile: in the three-necked bottle equipped with a magnetic stirring device, an airway, and a reflux device, add successively dry 3-nitro-o-phthalonitrile according to the molar ratio Phthalonitrile and 8-hydroxyquinoline 1~8: 1~6, and add potassium carbonate and 10~30ml: the amount of 1mol8-hydroxyquinoline adds solvent N according to the amount of 1~6mol: 1mol8-hydroxyquinoline, N-Dimethylformamide DMF, stirred, and reacted at 5-40°C for 3-12 hours under the protection of nitrogen; after the reaction, pour it into ice water, stir it thoroughly and filter it with suction, and wash the filter cake with distilled water to the filtrate The obtained solid is recrystallized several times with methanol to obtain a pink solid; the pink solid is dried and weighed, the yield is 75-85%, and the melting point is 212-213°C;

[0014] (2) Synthesis of zinc phthalocyanine complex: In a reac...

Embodiment 1

[0019] (1) Synthesis of 3-(8-quinolineoxy)phthalonitrile: Add dry 1.38g (8mmol) 3-nitrate in turn in a 100ml three-necked bottle equipped with a magnetic stirring device, an airway, and a reflux device Base phthalonitrile and 1.16g (8mmol) 8-hydroxyquinoline, 1g potassium carbonate and 10mlDMF, stirred, and reacted at 10°C for 5 hours under the protection of nitrogen. After the reaction was finished, it was poured into an appropriate amount of ice water, stirred thoroughly, and suction filtered, and the filter cake was washed with distilled water until the filtrate was neutral. The obtained solid was recrystallized several times with methanol to obtain a pink solid. After drying and weighing, the yield was 81%, and the melting point was 212-213°C.

[0020] (2) Synthesis of zinc phthalocyanine complex: Add 0.28g (1mmol) 3-(8-quinolineoxy) phthalonitrile and 1.15g (9mmol) o-phthalonitrile in sequence in a reaction vessel with a reflux condensing device Diformonitrile and 0.3ml ...

Embodiment 2

[0025] The preparation method is the same as in Example 1, in (1) process, the mol ratio of 3-nitrophthalonitrile and 8-hydroxyquinoline is changed into 2: 1, other operations are identical, 3-(8-quinoline The productive rate of oxygen) phthalonitrile is 78%; In (2) process, the mol ratio of 3-(8-quinolineoxy) phthalonitrile and phthalonitrile is changed into 1: 5. Other operations are the same as in Example 1, and the yield of the final target product is 26%.

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Abstract

The invention provided an alpha-(8-quinoly) single substituted zinc phthalocyanine and a preparation method thereof, with the molecular formula of C41H21N9OZn; the preparation method is as follows: 8-hydroxyl quinoly and 3- nitrophthalonitrile are adopted as the original substances to synthesize 3-(8- quinoly) phthalonitrile; then 3-(8- quinoly) phthalonitrile, phthalonitrile, and the corresponding zinc salt are adopted as the original substances to synthesize a coordination compound of Phthalocyanine-zinc under the DBU catalysis, and then the coordination compound of Phthalocyanine-zinc is separated to obtain the final product. The coordination compound provided by the invention has a single structure without any isomer, and is characterized in defined structure and easy separation. The coordination compound can be applied in the high-tech fields such as the preparation of novel anti-cancer drugs.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and more specifically relates to an α-(8-quinolineoxy) monosubstituted zinc phthalocyanine and a preparation method thereof. Background technique [0002] Because phthalocyanine is relatively easy to synthesize and has high stability, phthalocyanine is widely used in industry. In addition, there is a strong π-π in the visible region * transition, with good oxidation-reduction activity. Phthalocyanine has long been used as a dye and a petroleum desulfurization catalyst, and in recent years, it has been used as a photoconductive agent for photoreplication. Recently, the application of phthalocyanine in high-tech fields has become an emerging hotspot, including semiconductor devices, photovoltaics and solar cells, xerography, rectifiers, LB films, low-dimensional conductor materials, gas sensors, electrocatalysis, deodorants, Bactericides, photosensitizers for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07F3/06
Inventor 薛金萍刘宏方昱婷陈耐生黄金陵
Owner FUZHOU UNIV
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