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
View PDF0 Cites 4 Cited by
  • 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, molecul

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0030] Example 1:

[0031] Add 11.2g 4-dimethylaminobenzaldehyde, 350ml xylene, 0.25g dichloroacetic acid, 12g nitrobenzene into a 500ml four-necked flask, heat to 130℃, take another 100ml three-necked flask, add 178g pyrrole, and heat to At 60°C, nitrogen was introduced into the pyrrole, and the carrier gas containing pyrrole was introduced into the reaction system. The flow rate of the carrier gas was controlled at 2ml / s. The reaction time was 48h. The remaining pyrrole amount was 168g. Toluene, cooling, drying, Soxhlet extraction with methanol, until the outflow of methanol is almost colorless, take out tetra(4-dimethylaminophenyl) porphyrin, dry, crude weight 12.7g, crude yield 86%, by UV spectroscopy The content of tetrakis (4-dimethylaminophenyl) porphyrin in the crude product was determined, and the yield of tetrakis (4-dimethylaminophenyl) porphyrin was 57%.

Example Embodiment

[0032] Example 2:

[0033] Add 11.2g 4-dimethylaminobenzaldehyde, 350ml xylene, 0.37g dichloroacetic acid, 12g nitrobenzene into a 500ml four-necked flask, heat to 130℃, take another 100ml three-necked flask, add 170g pyrrole, and heat to At 60℃, pour nitrogen into the pyrrole and introduce the carrier gas containing pyrrole into the reaction system. The flow rate of the carrier gas is controlled at 1.2ml / s, the reaction is 48h, and the remaining amount of pyrrole is 160g. A total of 10g pyrrole is introduced and removed by rotary evaporation. Xylene, cooling, drying, Soxhlet extraction with methanol, until the outflow of methanol is almost colorless, take out tetrakis (4-dimethylaminophenyl) porphyrin, dry, crude weight 12.4, crude yield 84%, by UV spectroscopy The content of tetrakis (4-dimethylaminophenyl) porphyrin in the crude product was determined, and the yield of tetrakis (4-dimethylaminophenyl) porphyrin was 55%.

Example Embodiment

[0034] Example 3:

[0035]Add 11.2g 4-dimethylaminobenzaldehyde, 350ml xylene, 0.5g dichloroacetic acid, 12g nitrobenzene into a 500ml four-neck bottle, heat to 120℃, take another 100ml three-necked bottle, add 171g pyrrole, and heat to At 60°C, nitrogen was introduced into the pyrrole, and the carrier gas containing pyrrole was introduced into the reaction system. The flow rate of the carrier gas was controlled at 2ml / s. The reaction time was 48h. The remaining pyrrole amount was 161g. Toluene, cooling, drying, Soxhlet extraction with methanol, until the outflow of methanol is almost colorless, take out tetrakis (4-dimethylaminophenyl) porphyrin, dry, crude weight 10.4g, crude yield 71%, by UV spectroscopy The content of tetrakis (4-dimethylaminophenyl) porphyrin in the crude product was determined, and the yield of tetrakis (4-dimethylaminophenyl) porphyrin was 47%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D487/22
Inventor 孙哲牛国兴
Owner FUDAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap