Method for synthesizing ionic type metal porphyrin

A synthesis method and technology of metalloporphyrins, applied in the direction of organic chemistry, etc., can solve the problems of difficult porphyrin separation and purification, low separation yield, etc.

Inactive Publication Date: 2010-03-10
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The problem that this method exists is (1) in the process of synthesizing porphyrin by the condensation reaction of substituted formaldehyde and pyrrole, a lot of side reactions take place, and the polarity and solubility property of many by-products are similar to porphyrin
Therefore, the separation and purification of porphyrin are very difficult work, and the separation yield is low; (2) noble metal ions such as Au 3+ , Pd 2+ , or Pt 2+ It is difficult to directly coordinate with porphyrin. Usually, it is necessary to use zinc salt as the template center or under strong basic conditions to insert the above transition metal ions into the porphine ring to form the corresponding metalloporphyrin
However, under strong alkaline conditions, metalloporphyrins can easily form μ-oxymetalloporphyrin dimers.

Method used

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  • Method for synthesizing ionic type metal porphyrin
  • Method for synthesizing ionic type metal porphyrin
  • Method for synthesizing ionic type metal porphyrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 500mL propionic acid, 12.8g 4-pyridine formaldehyde, and 8.0g pyrrole in a 1000mL three-necked flask, and reflux for 2.5h. After the reaction is completed, remove most of the propionic acid by rotary evaporation, then add 600mL ethanol, cool and recrystallize to obtain four Pyridyl porphyrin, the yield is 26.0%. The product was added with 50 mL of N, N-dimethylformamide, and excess iodomethane, refluxed for 2 hours, and the reaction mixture was filtered to obtain tetrakis-(N-methyl-4-pyridyl)porphyrin iodide salt with a yield of 90.2%. The obtained solid was dissolved in 50 mL of deionized water, an excess of manganese acetate was added, refluxed for 2 hours, and then ammonium hexafluorophosphate was added, and the obtained solid was precipitated as tetrakis-(N-methyl-4-pyridyl)manganese porphyrin hexafluorophosphate , yield 99.0%.

Embodiment 2

[0027] Dissolve the tetrakis-(N-methyl-4-pyridyl)porphyrin iodide salt synthesized according to the steps of Example 1 in 50 mL of deionized water, add excess palladium chloride, reflux for 2 hours, cool and filter to remove the excess insoluble metal salt , ammonium hexafluorophosphate was added to the filtrate, and the precipitate was tetrakis-(N-methyl-4-pyridyl)palladium porphyrin hexafluorophosphate, with a yield of 92.0%.

Embodiment 3

[0029] The four-(N-methyl-4-pyridyl) porphyrin iodide salt synthesized according to the steps of Example 1 was dissolved in 50 mL of deionized water, an excess of platinum chloride was added, refluxed for 2 hours, cooled and filtered to remove the excess metal salt, Ammonium hexafluorophosphate was added to the filtrate, and the precipitate was tetrakis-(N-methylpyr-4-idinyl)palladium porphyrin hexafluorophosphate, with a yield of 93.0%.

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Abstract

The invention relates to a method for synthesizing ionic type metal porphyrin, in particular to a method which is used for synthesizing ionic type metal porphyrin by taking nitrogen-containing heterocyclic aryl formaldehyde and pyrrole as raw materials. The method takes the nitrogen-containing heterocyclic aryl formaldehyde and the pyrrole as raw materials, and comprises the following steps of: firstly, synthesizing neutral porphyrin free alkali; then, halogenated alkane and the porphyrin free alkali are subject to quaternization reaction, and synthesizing corresponding ionic type porphyrin free alkali; finally, under the alkalescent or neutral condition, mixing the ionic type porphyrin free alkali and transition metal salt, and synthesizing ionic type metal aryl porphyrin under the heating condition. By adopting the three-step method to synthesize the ionic type metal porphyrin, the purification process of metal porphyrin compound is greatly simplified, the yield of product is improved; and compared with the traditional neutral porphyrin, the ionic type porphyrin free alkali synthesized by the method can coordinate with transition metal ions under the mild condition.

Description

technical field [0001] The invention relates to a method for synthesizing ionic metalloporphyrin, in particular to a method for synthesizing ionic metalloporphyrin by using nitrogen-containing heterocyclic aryl formaldehyde and pyrrole as raw materials. Background technique [0002] Metalloporphyrins are widely found in living organisms in nature and play an important role in life activities. Chlorophyll, heme, vitamin B12, etc. can all be regarded as metalloporphyrin compounds, which are responsible for oxygen transfer (hemoglobin), storage (myoglobin), activation (cytochrome P-450) and photosynthesis in the life process (chlorophyll) and so on play a very important role. Through the study of metalloporphyrin structure, spectral characteristics, electrochemical properties and photochemistry, it is found that metalloporphyrin has a wide range of applications in biochemistry, medicinal chemistry, photochemistry, analytical chemistry, catalytic chemistry and so on. At presen...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 刘晔刘伟张静周成亮王洒洒
Owner EAST CHINA NORMAL UNIVERSITY
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