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Synthesis method of tetra (4-aminophenyl) porphyrin metal complex

A technology of metal complexes and synthesis methods, applied in the field of polymer synthesis, can solve problems such as environmental pollution, and achieve the effects of high yield, mild reaction conditions and low cost

Active Publication Date: 2021-06-11
中国人民解放军军事科学院防化研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Based on the above problems, the object of the present invention is to provide a synthetic method of tetrakis (4-aminophenyl) porphyrin metal complexes, the method is more mild than the traditional preparation method reaction conditions, the reagents used are less toxic , the whole preparation route is more green and environmentally friendly, which can solve the problem that toxic and harmful reagents such as nitrobenzene and concentrated hydrochloric acid are likely to cause environmental pollution in the current preparation process of tetrakis (4-aminophenyl) porphyrin metal complexes; at the same time, the obtained The product has a higher yield

Method used

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  • Synthesis method of tetra (4-aminophenyl) porphyrin metal complex

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Synthesis of tetrakis(4-aminophenyl)copper porphyrin

[0046] Weigh 7.40g (0.04mol) of p-bromobenzaldehyde, dissolve it in 30ml of propionic acid, add it dropwise to the refluxing 100ml of propionic acid simultaneously with 20ml of propionic acid solution containing 2.80ml of pyrrole (0.04mol), and continue to Reflux reaction for 30min, after being cooled to room temperature, put it into a refrigerator to stand overnight, filter with suction, wash the filter cake with methanol, then wash with water, then wash with methanol, and obtain tetrakis(4-bromophenyl)porphyrin after vacuum drying. 1.86 g, 20% yield.

[0047] Weigh 93 mg (0.1 mmol) of tetrakis(4-bromophenyl)porphyrin, dissolve it in 150 ml of a mixed solvent of chloroform and N,N-dimethylformamide, and heat it to 50°C with stirring under nitrogen protection. Weigh 30mg (0.15mmol) of copper acetate monohydrate, dissolve it in 10ml of methanol, add the methanol solution of copper acetate to the porphyrin solution d...

Embodiment 2

[0050] Synthesis of tetrakis(4-aminophenyl)zinc porphyrin

[0051] Weigh 9.28g (0.04mol) of p-iodobenzaldehyde, dissolve it in 30ml of propionic acid, add it dropwise to the refluxing 100ml of propionic acid simultaneously with 20ml of propionic acid solution containing 2.80ml of pyrrole (0.04mol), and continue to Reflux reaction for 30min, after being cooled to room temperature, put it into the refrigerator to stand overnight, filter with suction, wash the filter cake with methanol, then wash with water, then wash with methanol, and obtain tetrakis(4-iodophenyl)porphyrin after vacuum drying. 2.15 g, 18% yield.

[0052] Weigh 112 mg (0.1 mmol) of tetrakis(4-iodophenyl)porphyrin, dissolve it in 150 ml of a mixed solvent of chloroform and N,N-dimethylformamide, and heat it to 50°C with stirring under nitrogen protection. Weigh 33mg (0.15mmol) of zinc acetate dihydrate, dissolve it in 10ml of methanol, add the methanol solution of copper acetate to the porphyrin solution dropwis...

Embodiment 3

[0055] Synthesis of tetrakis(4-aminophenyl)nickel porphyrin

[0056] Weigh 112 mg (0.1 mmol) of tetrakis(4-iodophenyl)porphyrin, dissolve it in 150 ml of a mixed solvent of chloroform and N,N-dimethylformamide, and heat it to 50°C with stirring under nitrogen protection. Weigh 37.3mg (0.15mmol) of nickel acetate tetrahydrate, dissolve it in 10ml of methanol, add the methanol solution of nickel acetate dropwise to the porphyrin solution, raise the temperature to 100°C, and react for 24 hours, concentrate the reaction solution by rotary evaporation, add methanol to Crystallized and filtered to obtain dark red tetrakis (4-iodophenyl) nickel porphyrin 110.5mg, yield 94%.

[0057] Using a pressure bottle as a container, weigh 58.8 mg (0.05 mmol) of tetrakis(4-iodophenyl) nickel porphyrin, 13 mg of copper acetylacetonate, 10 μL of acetylacetone, and 42 mg of anhydrous potassium phosphate, and dissolve them in 15 ml of N-methylpyrrolidone After vacuuming, 0.35ml of concentrated ammo...

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Abstract

The invention discloses a synthesis method of a tetra (4-aminophenyl) porphyrin metal complex. The method comprises the following steps: 1) taking organic acid as a solvent and pyrrole and 4-halogen benzaldehyde as substrates, and carrying out condensation reaction to obtain a (4-halogen phenyl) porphyrin solid; 2) dissolving the (4-halogen phenyl) porphyrin solid in an organic solvent, adding a metal salt, and reacting to obtain a (4-halogen phenyl) porphyrin metal complex; and 3) taking the (4-halophenyl) porphyrin metal complex and ammonia water as substrates, and carrying out carbon-nitrogen coupling reaction in the presence of a catalyst and an organic solvent to obtain the tetra (4-aminophenyl) porphyrin metal complex. The method is mild in reaction condition, low in toxicity, green and environment-friendly.

Description

technical field [0001] The present invention relates to the field of polymer synthesis. More specifically, it relates to a method for synthesizing tetrakis(4-aminophenyl)porphyrin metal complexes. Background technique [0002] Porphyrin and its derivatives are a class of important life substances that widely exist in nature. The basic structure of this type of compound is a porphine nucleus, which is composed of four pyrrole rings through four sp 2 It has a planar ring structure formed by alternately connecting carbon atoms with 18π electron conjugated system, and the four nitrogen atoms in the hole surrounded by the middle pyrrole ring can complex with almost all metal ions in the periodic table to form a stable Complexes. The two most typical representatives of these complexes are chlorophyll, a derivative of magnesium porphyrin, and heme, a derivative of iron porphyrin, which play important roles in the two key life processes of storing energy and releasing energy, resp...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22Y02E10/549
Inventor 曹韡丁志军郑永超杜斌陈东陈茜李志军
Owner 中国人民解放军军事科学院防化研究院
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