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Carboxyl porphyrin and preparation method thereof

A technology of carboxyl porphyrin and ester porphyrin, which is applied in the field of preparation of carboxyl porphyrins connected by different alkoxy groups, can solve the problems of low yield of asymmetric carboxyl porphyrin and the like, and achieves high yield and simple reaction steps. Effect

Inactive Publication Date: 2010-03-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the traditional Alder synthesis method is to directly synthesize carboxyporphyrin from pyrrole and carboxybenzaldehyde, or to synthesize porphyrin with ester benzaldehyde instead of carboxybenzaldehyde and then hydrolyze it. The carboxyporphyrin obtained by this method is linked to benzene The ring is only one carboxyl group, and the yield is extremely low when synthesizing asymmetric carboxyporphyrin

Method used

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  • Carboxyl porphyrin and preparation method thereof
  • Carboxyl porphyrin and preparation method thereof
  • Carboxyl porphyrin and preparation method thereof

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Embodiment 15

[0032] The preparation of embodiment 15-(4-hydroxymethyleneoxy) phenyl-10,15,20-triphenylporphyrin

[0033] The preparation method of the present embodiment 5-(4-hydroxymethyleneoxy)phenyl-10,15,20-triphenylporphyrin comprises the following steps:

[0034] (1) Add 0.189g 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin, 1.5mL ethyl 2-bromoacetate (hydroxyporphyrin and 2-bromoacetic acid) to the round bottom flask The molar ratio of ethyl ester is 1:45), 45mL DMF, 1.8g freshly roasted K 2 CO 3 , after stirring and reacting at 100°C for 9 hours, stop the reaction, add deionized water and chloroform to the reaction solution for extraction, extract 4 times, and spin dry to obtain 5-(4-carboxymethyleneoxyethyl ester) Phenyl-10,15,20-triphenylporphyrin crude product;

[0035] (2) Dissolve the crude product of 5-(4-carboxymethyleneoxyethyl)phenyl-10,15,20-triphenylporphyrin obtained in step (1) into 10 mL of chloroform, add 10% KOH methanol solution 10 mL, stirred at room temperat...

Embodiment 25

[0037] Preparation of Example 25-(4-carboxymethyleneoxy)phenyl-10,15,20-three(4-tolyl)porphyrin

[0038] The preparation method of the present embodiment 5-(4-carboxymethyleneoxy)phenyl-10,15,20-tri(4-tolyl)porphyrin comprises the following steps:

[0039] (1) Add 0.206g 5-(4-hydroxyphenyl)-10,15,20-tri(4-methylphenyl)porphyrin, 1.5mL ethyl 2-bromoacetate (hydroxyporphyrin and The molar ratio of ethyl 2-bromoacetate is 1:44), 45mL DMF, 1.8g freshly roasted K 2 CO 3 , after stirring for 9 hours at 100°C, stop the reaction, add deionized water and chloroform to the reaction solution for extraction, extract 4 times, and spin dry to obtain 5-(4-carboxymethyleneoxyethyl)phenyl-10 , 15,20-three (4-tolyl) porphyrin crude product;

[0040] (2) Dissolve the crude product of 5-(4-carboxymethyleneoxyethyl ester) phenyl-10,15,20-tri(4-methylphenyl)porphyrin prepared in step (1) into 10 mL of chloroform, add 10 mL of 10% KOH methanol solution was stirred at room temperature for 0.5 h, ...

Embodiment 35

[0042] Preparation of Example 35-(4-carboxymethyleneoxy)phenyl-10,15,20-three(4-chlorophenyl)porphyrin

[0043] The preparation method of the present embodiment 5-(4-carboxymethyleneoxy)phenyl-10,15,20-tri(4-chlorophenyl)porphyrin comprises the following steps:

[0044] (1) Add 0.192g 5-(4-hydroxyphenyl)-10,15,20-tris(4-chlorophenyl)porphyrin, 1.5mL ethyl 2-bromoacetate (hydroxyporphyrin) to the round bottom flask The molar ratio to ethyl 2-bromoacetate is 1:52), 45mL DMF, 1.8g freshly roasted K 2 CO 3 , Stirring at 100°C for 9h. Stop the reaction, add deionized water and chloroform for extraction, extract 4 times, and spin dry to obtain 5-(4-carboxymethyleneoxyethyl)phenyl-10,15,20-tri(4-chlorophenyl) Crude product of porphyrin;

[0045] (2) Dissolve the crude product of 5-(4-carboxymethyleneoxyethyl)phenyl-10,15,20-tris(4-chlorophenyl)porphyrin prepared in step (1) into 10 mL of chloroform, 10 mL of methanolic 10% KOH was added. After stirring at room temperature for 0...

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Abstract

The invention discloses a carboxyl porphyrin and preparation method thereof, wherein the carboxyl porphyrin has a general formula represented by formula (1) in which R1 represents -H, -CH3, -OCH3, -C1, -F or -NO2; R2 represents -O(CH2)nCOOH (n=1, 3, 5 or 6); or, R1=R2=-O(CH2)nCOOH (n=1, 3, 5 or 6). According to the invention, hydroxylporphyrin having phenolic hydroxyl is reacted with n-bromoacid ethyl ester so as to synthesize ester-based porphyrin, and then carboxyl porphyrin can be obtained by hydrolyzing ester-based porphyrin. The method can be used for obtaining different types of symmetrical or asymmetrical carboxyl porphyrin having alkoxyls in different connection with carboxyl by changing different substituents of hydroxylporphyrin and changing the type of n-bromoacid ethyl ester, wherein the reaction steps are simple and the yield thereof is high.

Description

technical field [0001] The invention relates to the field of chemical synthesis of macromolecules, in particular to a carboxyporphyrin linked by different alkoxy groups and a preparation method thereof. Background technique [0002] Porphyrin is a general term for porphine derivatives, metal ions embedded in porphyrin rings can form stable metal porphyrin complexes. Porphyrin compounds have a special structure of large conjugated planes, which have both electron-donating and electron-accepting properties. The unique structure, superior physical, chemical and optical characteristics of porphyrin compounds make porphyrin compounds have very broad applications in bionics, materials chemistry, medicinal chemistry, electrochemistry, photophysics and chemistry, analytical chemistry, organic chemistry and other fields. The application prospect attracts people to study in depth continuously. [0003] By introducing different functional groups on the porphyrin ring, many porphyrin ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
Inventor 黄锦汪叶元坚罗海英余汉城计亮年
Owner SUN YAT SEN UNIV