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Preparation method for tetra-(o-pivaloyl amino phenyl) zinc protoporphyrin isomer compound

A technology of pivalamidophenyl and nitrophenylporphyrin, which is applied in the field of preparation of four isomer compounds, can solve the problem of easy isomerization, rare and difficult to obtain four pure isomers Compounds and other problems, to achieve the effect of high yield and simple synthesis method

Inactive Publication Date: 2012-03-28
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Tetrakis-(o-pivalamidophenyl)porphyrin zinc compound is an ideal gas sensing material with high research value, but because it contains four isomers with similar properties, it is very easy to isomerize According to the traditional metalloporphyrin synthesis method, the mixture of its four isomers is obtained, and it is difficult to obtain its four pure isomer compounds, and there are few reports in this regard at home and abroad.

Method used

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  • Preparation method for tetra-(o-pivaloyl amino phenyl) zinc protoporphyrin isomer compound

Examples

Experimental program
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Effect test

Embodiment 1

[0020] (1) In a 100ml three-neck flask, add 80ml of concentrated hydrochloric acid, 1.613g of NO 2 PP, 6.721g SnCl 2 2H 2 O, install a reflux condenser, a thermometer, magnetically stir, rapidly raise the temperature to 70°C, react for 30 minutes, stop the reaction, CHCl 3 Extraction and liquid separation, organic phase rotary evaporation to obtain NH 2 The crude PP solid product was separated by column with petroleum ether and ethyl acetate 5:1 as eluent, and different purple bands were collected, and the solvent was removed by rotary evaporation at low temperature to obtain αβαβ-NH 2 PP, ααββ-NH 2 PP, αααβ-NH 2 PP, αααα-NH 2 PP four compounds, a total of 1.334g, yield 92.0%.

[0021] (2) Add 0.507g αβαβ-NH to a 100ml three-neck flask 2 PP, 30mlCH 2 Cl 2 , install a reflux condenser, a thermometer, magnetically stir, cool in an ice-water bath, control the temperature below 5°C, add a little excess pivaloyl chloride and pyridine dropwise, react for one hour, stop the ...

Embodiment 2

[0024] (1) In a 100ml three-neck flask, add 80ml of concentrated hydrochloric acid, 1.659gNO 2 PP, 6.724g SnCl 2 2H 2 O, install a reflux condenser, a thermometer, magnetically stir, rapidly raise the temperature to 70°C, react for 30 minutes, stop the reaction, CHCl 3 Extraction, organic phase rotary evaporation to obtain NH 2 The crude PP solid product was separated by column with petroleum ether and ethyl acetate 5:1 as eluent, and different purple bands were collected, and the solvent was removed by rotary evaporation at low temperature to obtain αβαβ-NH 2 PP, ααββ-NH 2 PP, αααβ-NH 2 PP, αααα-NH 2 PP four compounds, a total of 1.396g, yield 93.1%.

[0025] (2) Add 0.513g αβαβ-NH to a 100ml three-neck flask 2 PP, 30mlCH 2 Cl 2 , install a reflux condenser, a thermometer, magnetically stir, cool in an ice-water bath, control the temperature below 5°C, add a little excess pivaloyl chloride and pyridine dropwise, react for one hour, stop the reaction, and rotate at a ...

Embodiment 3

[0028] (1) In a 100ml three-neck flask, add 80ml of concentrated hydrochloric acid, 1.623g of NO 2 PP, 6.750g SnCl 2 2H 2 O, install a reflux condenser, a thermometer, magnetically stir, rapidly raise the temperature to 70°C, react for 30 minutes, stop the reaction, CHCl 3 Extraction, organic phase rotary evaporation to obtain NH 2 The crude PP solid product was separated by column with petroleum ether and ethyl acetate 5:1 as eluent, and different purple bands were collected respectively, and the solvent was removed by rotary evaporation at low temperature to obtain αβαβ-NH 2 PP, ααββ-NH 2 PP, αααβ-NH 2 PP, αααα-NH 2 PP four compounds, a total of 1.373g, yield 93.6%.

[0029] (2) Add 0.504g ααββ-NH to a 100ml three-neck flask 2 PP, 30mlCH 2 Cl 2 , install a reflux condenser, a thermometer, magnetically stir, cool in an ice-water bath, control the temperature below 5 degrees, add a little excess pivaloyl chloride and pyridine dropwise, react for one hour, stop the rea...

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Abstract

The invention relates to a preparation method for tetra-(o-pivaloyl amino phenyl) zinc protoporphyrin isomer compound, which comprises the following steps: by taking tetra-o-chloronitrobenzene protoporphyrin as a raw material and utilizing a three-step method, controlling the use amount of the raw material, reaction temperature and solvent selection to respectively synthesize four tetra-(o-pivaloyl amino phenyl) zinc protoporphyrin isomer compounds with extra high purity, wherein the tetra-(o-Pivaloyl amino phenyl) zinc protoporphyrin isomer compounds have the formula disclosed in (I). According to the preparation method, the purification process of the metal protoporphyrin compound containing the isomer is greatly simplified, and the preparation method is simple to operate and has the advantages of available raw material and high yield.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of four isomer compounds of tetrakis-(o-pivalamidophenyl) porphyrin zinc. Background technique [0002] Porphyrin was first proposed by Kuster in 1912. It is a class of macrocyclic compounds composed of four pyrrole rings connected by methine to form a conjugated skeleton. They have a rigid conjugated ring structure and are highly adjustable. The electron mobility is good, the ring plane is easy to modify, and it also shows good thermal stability and photoelectric performance. Therefore, the research on porphyrin and its metal complexes with special functional properties is a hot spot in the field of porphyrin chemistry in recent years. With the in-depth research on porphyrins and metalloporphyrins, they are playing an increasingly important role in the research of bionics, catalysis, medicine, analytical chemistry, coordination chemistry, etc. In 2000, Pro...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 任玉杰查甫德陈启斌焦家俊
Owner EAST CHINA UNIV OF SCI & TECH
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