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Synthetic method for metal porphyrin

A synthesis method and metalloporphyrin technology are applied in chemical instruments and methods, compounds of Group 7/17 elements of the periodic table, compounds containing elements of Group 8/9/10/18 of the periodic table, etc., and the steps are simple. Effect

Inactive Publication Date: 2007-04-11
BEIJING UNIV OF TECH
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  • Claims
  • Application Information

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Problems solved by technology

The problem that this method exists is: (1) the organic solvent that adds is single solvent (see embodiment 1~6 and 8~10); (2) adopts two-step synthesis; (3) needs to add zinc salt as template Center; (4) yield is only 20~40%

Method used

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  • Synthetic method for metal porphyrin
  • Synthetic method for metal porphyrin

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Embodiment 1

[0016] In a 250mL three-necked flask, add 60mL propionic acid, 20mL glacial acetic acid and 20mL nitrobenzene (the weight percentage of the three is respectively 57%, 20%, 23%) mixed solvent, then add 10mmol benzaldehyde and 10mmol pyrrole, after , add 0.7g manganese acetate, heat to reflux for 1h, cool, add 30mL of methanol, stir, let stand overnight, and suction filter to get tetraphenylmanganese porphyrin (i.e. R in general formula (I) 1 = H, R 2 =H, M=Mn), weighed after drying, the yield was 57.6%, and its purity was 99.7% as detected by liquid chromatography.

Embodiment 2

[0018] In a 250mL three-necked flask, add 60mL propionic acid, 20mL glacial acetic acid and 20mL m-nitrotoluene (the weight percentage of the three is respectively 58%, 20%, 22%) mixed solvent, then add 10mmol p-nitrobenzaldehyde and 10mmol pyrrole, after that, add 0.7g ferrous acetate, heat and reflux 1h, cool, add 30mL methanol, stir, stand overnight, suction filtration, get tetra-(p-nitrophenyl)iron porphyrin (being general formula ( I) Medium R 1 = NO 2 , R 2 =H, M=Fe), weighed dry, its yield was 41.5%, and its purity was 99.8% as detected by liquid chromatography.

Embodiment 3

[0020] In the 250mL three-necked flask, add 70mL n-hexanoic acid and 30mL formic acid (the percentage by weight of the two is respectively 65%, 35%) mixed solvent, then add 10mmol p-chlorobenzaldehyde and 10mmol pyrrole, after that, add 0.7g copper acetate, Heated to reflux for 1h, cooled, added 30mL of methanol, stirred, left to stand overnight, and suction filtered to obtain tetra-(p-chlorophenyl)copper porphyrin (i.e. R in general formula (I) 1 = Cl, R 2 =H, M=Cu), weighed dry, its yield was 53.4%, and its purity was 99.9% as detected by liquid chromatography.

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Abstract

The present invention is method of synthesizing metalloporphyrin. Into the mixed solvent comprising two kinds of C1-C8 straight chain fatty acid and nitrobenzene or nitrobenzene derivative, substituted benzaldehyde and pyrrole and soluble transition metal salt are added and reacted through heating reflux for 0.5-1 hr to obtain metalloporphyrin in one reaction step. In the reaction system, the weight ratio between two kinds of straight chain fatty acid is 10-85 %, and the weight fraction of nitrobenzene or nitrobenzene derivative is 0-25 %. Compared with available technology, the present invention has the advantages of capacity of synthesizing several kinds of metalloporphyrin without need of soluble zinc salt, short reaction period and high yield up to 40-60 %.

Description

technical field [0001] The invention relates to a method for synthesizing metalloporphyrins. Background technique [0002] Metalloporphyrins have unique structures, superior physical, chemical and optical characteristics, which make them have very broad application prospects in biomimetic chemistry, material chemistry, photoelectric conversion, medicinal chemistry, analytical chemistry, organic chemistry and other fields. The current method for synthesizing metalloporphyrins is mainly a two-step method, that is, pyrrole and (substituted) benzaldehyde are condensed to generate porphyrins, and then porphyrins react with metal salts to generate metalloporphyrins. Chinese patent CN 1238355C (authorized announcement date: January 25, 2006) discloses a synthesis method of metalloporphyrins, which is also synthesized by a two-step method, firstly adding pyrrole, aromatic aldehyde and soluble zinc salt to the organic solvent , to obtain a mixture of aryl porphine and zinc aryl porp...

Claims

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Application Information

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IPC IPC(8): C07F15/00C07F3/06C07F1/08C07F13/00C07D487/22
Inventor 佘远斌孙志成张天慧王兰芝钟儒刚
Owner BEIJING UNIV OF TECH
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