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Synthesis method of tetra (4-dimethylaminophenyl) porphyrin and derivatives thereof

A technology of dimethylaminophenyl and trimethylaminophenyl, which is applied in the field of synthesizing tetraporphyrin and its derivatives, can solve the problem of synthesizing tetrakis(4-trimethylaminophenyl)porphyrin hydroxide. Issues such as reporting, application scope, and in-depth research limitations, preparation of special materials and functional devices, etc., to achieve the effects of improving synthesis efficiency, increasing yield, and increasing reaction yield

Inactive Publication Date: 2009-12-30
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Tetraphenylporphyrin is the earliest synthesized and most researched porphyrin, but due to its poor water solubility and no polar or ionic groups on the benzene ring, it is impossible to prepare some special materials through functional grafting, molecular assembly and other follow-up work and functional devices, so that its application range and in-depth research are greatly limited
[0006] There are no literature reports on the synthesis of tetrakis(4-trimethylaminophenyl)porphyrin hydroxide at home and abroad

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 11.2g of 4-dimethylaminobenzaldehyde, 350ml of xylene, 0.25g of dichloroacetic acid, and 12g of nitrobenzene into a 500ml four-necked bottle, and heat to 130°C. Take another 100ml three-necked bottle, add 178g of pyrrole, and heat to 60°C, feed nitrogen into the pyrrole, and introduce the carrier gas loaded with pyrrole into the reaction system. The carrier gas flow rate is controlled at 2ml / s. After 48 hours of reaction, the remaining amount of pyrrole is 168g, and a total of 10g of pyrrole is introduced. Toluene, cooled, dried, carried out Soxhlet extraction with methanol, until the eluting methanol was nearly colorless, took out tetrakis (4-dimethylaminophenyl) porphyrin, dried, crude weight 12.7g, crude yield 86%, through ultraviolet spectrum The content of tetrakis(4-dimethylaminophenyl)porphyrin in the crude product was determined, and the yield of tetrakis(4-dimethylaminophenyl)porphyrin was 57%.

Embodiment 2

[0033] Add 11.2g of 4-dimethylaminobenzaldehyde, 350ml of xylene, 0.37g of dichloroacetic acid, and 12g of nitrobenzene into a 500ml four-necked bottle, and heat to 130°C. Take another 100ml three-necked bottle, add 170g of pyrrole, and heat to 60°C, feed nitrogen into the pyrrole, and introduce the carrier gas loaded with pyrrole into the reaction system. The carrier gas flow rate is controlled at 1.2ml / s. After 48 hours of reaction, the remaining amount of pyrrole is 160g, and a total of 10g of pyrrole is introduced. Xylene, cooled, dried, carried out Soxhlet extraction with methanol, until the effluent methanol was nearly colorless, took out tetrakis (4-dimethylaminophenyl) porphyrin, dried, crude weight 12.4, crude yield 84%, through ultraviolet spectrum The content of tetrakis(4-dimethylaminophenyl)porphyrin in the crude product was measured, and the yield of tetrakis(4-dimethylaminophenyl)porphyrin was 55%.

Embodiment 3

[0035]Add 11.2g of 4-dimethylaminobenzaldehyde, 350ml of xylene, 0.5g of dichloroacetic acid, and 12g of nitrobenzene into a 500ml four-necked bottle, and heat to 120°C. Take another 100ml three-necked bottle, add 171g of pyrrole, and heat to 60°C, feed nitrogen into the pyrrole, and introduce the carrier gas loaded with pyrrole into the reaction system. The carrier gas flow rate is controlled at 2ml / s. After 48 hours of reaction, the remaining amount of pyrrole is 161g, and a total of 10g of pyrrole is introduced. Toluene, cooled, dried, carried out Soxhlet extraction with methanol, until the eluting methanol was nearly colorless, took out tetrakis (4-dimethylaminophenyl) porphyrin, dried, crude weight 10.4g, crude yield 71%, through ultraviolet spectrum The content of tetrakis(4-dimethylaminophenyl)porphyrin in the crude product was measured, and the yield of tetrakis(4-dimethylaminophenyl)porphyrin was 47%.

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PUM

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Abstract

The invention relates to a synthesis method of tetra(4-dimethylaminophenyl)porphyrin and derivatives thereof and belongs to the field of organic chemistry, comprising the following steps: adopting xylene as solvent, adding 4-dimethylaminobenzaldehyde in the presence of substituted acetic acid and nitrobenzene, introducing pyrrole with carrier gas, adopting methanol for performing Soxhlet extraction, drying the extracted product to obtain the desired tetra(4-dimethylaminophenyl)porphyrin; methylating tetra(4-dimethylaminophenyl)porphyrin in a reaction kettle to obtain tetra(4-trimethylaminophenyl)porphyrin iodide; converting tetra(4-trimethylaminophenyl)porphyrin iodide to tetra(4-trimethylaminophenyl)porphyrin hydroxide with anion exchange resin. The introduced pyrrole in the preparation method of the invention is uniform and is controlled to low concentration, thus reducing the self polymerization of pyrrole, improving the yield to be up to 57%, and significantly reducing the dosage of methyl iodide which is toxic and expensive; the product yield is increased by 10% compared with the prior art, and the resin used in the preparation method can be reused, so that the method is economic and environmentally friendly.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a method for synthesizing tetrakis(4-dimethylaminophenyl)porphyrin and derivatives thereof. Background technique [0002] Porphyrin compound is a general term for homologues and derivatives of porphine rings with substituents. Its parent structure is a conjugated macrocycle composed of 20 carbon atoms and 4 nitrogen atoms. The two protons on the nitrogen are covered by metal After substitution, metalloporphyrins can be formed, which will produce special optical properties, catalytic activity and physiological activity. Therefore, porphyrins and metalloporphyrins are used as complexing agents, photosensitizers, catalysts and sensors in medicinal chemistry, biomimetic catalysis, and materials chemistry. , Analytical chemistry and biochemistry and other fields have very good application prospects. [0003] Tetraphenylporphyrin is the earliest synthesized and most researched porphyr...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 孙哲牛国兴
Owner FUDAN UNIV
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