Flexible multi-arm porphyrin with pyridine groups and synthesis method thereof

A pyridine group, synthesis method technology, applied in flexible multi-arm porphyrin and its synthesis, flexible multi-arm porphyrin with pyridine group and its synthesis field, to achieve convenient operation, high yield and good coordination ability. Effect

Inactive Publication Date: 2011-08-31
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, flexible multi-armed porphyrins with pyridine groups have not been reported

Method used

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  • Flexible multi-arm porphyrin with pyridine groups and synthesis method thereof
  • Flexible multi-arm porphyrin with pyridine groups and synthesis method thereof
  • Flexible multi-arm porphyrin with pyridine groups and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

[0037] Add 9.1637g (75mmol) of m-hydroxybenzaldehyde to 100ml of propionic acid. After the temperature of the system reaches 130°C, add 5.3ml (75mmol) of pyrrole, reflux for 1h under nitrogen protection, cool to room temperature, stir for 24h, and filter. Rinse with hot distilled water at 80°C, dry in the air overnight, and separate by column chromatography (silica gel as stationary phase, chloroform / methanol (volume ratio: 9:1) as eluent), collect 5,10, 15,20-Tetrakis(3-hydroxyphenyl)porphyrin, 10% yield.

[0038] (2) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenylzinc)porphyrin

[0039] Add 0.4g (0.059mmol) of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin and 0.9g (0.47mmol) of zinc acetate to the mixed solution of chloroform and methanol (the volume ratio of the two is 1:1), reacted at 65°C for 3 hours, after the reaction was completed, the solvent was removed, and the crude product was separated by ...

Embodiment 2

[0044](1) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

[0045] Add 9.1637g (75mmol) of m-hydroxybenzaldehyde to 100ml of propionic acid. After the temperature of the system reaches 140°C, add 5.3ml (75mmol) of pyrrole, reflux for 2h under the protection of nitrogen, cool to room temperature, stir for 20h, and filter. Rinse with hot distilled water at 80°C, dry in the air overnight, separate by column chromatography (silica gel as stationary phase, use chloroform / methanol (volume ratio 9:1) as eluent), collect 5,10,15 , 20-tetrakis (3-hydroxyphenyl) porphyrin, yield 6.5%.

[0046] (2) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenylzinc)porphyrin

[0047] Add 0.4g (0.059mmol) of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin and 0.9g (0.47mmol) of zinc acetate to the mixed solution of chloroform and methanol (the volume ratio of the two is 1:1.5), reacted at 70°C for 4 hours, after the reaction was completed, the solvent was removed, and the crude product was se...

Embodiment 3

[0051] (1) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin

[0052] Add 9.1637g (75mmol) of m-hydroxybenzaldehyde to 100ml of propionic acid. After the temperature of the system reaches 130°C, add 8ml (112.5mmol) of pyrrole, reflux for 1h under nitrogen protection, cool to room temperature, stir for 24h, and filter. Rinse with hot distilled water at 80°C, dry in the air overnight, separate by column chromatography (silica gel as stationary phase, use chloroform / methanol (volume ratio 9:1) as eluent), collect 5,10,15 ,20-Tetrakis(3-hydroxyphenyl)porphyrin, yield 7%.

[0053] (2) Synthesis of 5,10,15,20-tetrakis(3-hydroxyphenylzinc)porphyrin

[0054] Add 0.4g (0.059mmol) of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin and 0.45g (0.24mmol) of zinc acetate into the mixed solution of chloroform and methanol (the volume ratio of the two is 1:2), reacted at 70°C for 4 hours, after the reaction was completed, the solvent was removed, and the crude product was separated b...

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PUM

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Abstract

The invention provides flexible multi-arm porphyrin with pyridine groups, and belongs to the technical field of chemical synthesis. M-hydroxy-benzaldehyd and pyrrole are taken as raw materials and subjected to three reactions of condensation, coordination and substitution to be successfully synthesized into 5,10,15,20-tetra{3-(4-methyleneoxy)pyridyl}phenyl zinc porphyrin. The compound has a plurality of flexible pyridine groups, and has good coordination capacity, so a series of metal coordination compounds can be derived from the compound serving as a raw material. The synthesis process is simple, the process route is short, and the operation is convenient; and the reaction conditions are mild, the cost is low and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a flexible multi-arm porphyrin and a synthesis method thereof, in particular to a flexible multi-arm porphyrin with a pyridine group and a synthesis method thereof. Background technique [0002] Porphine is a macromolecule with a planar conjugated ring structure formed by connecting four pyrrole rings through methine groups. When the hydrogen atoms on the porphine ring are partially or completely replaced by other atoms or groups, The resulting series of porphine derivatives are collectively referred to as porphyrins. Porphyrin compounds with planar large ∏ conjugated structures are stable against light and heat. Porphyrins have many unique physical properties, chemical behaviors, and other functional properties, such as photoelectric conversion, catalytic materials for solar energy storage, and microanalysis. [0003] The porphyrin structure can be simply modified wit...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 楚朝霞陈立伟洪慧琴刘家成
Owner NORTHWEST NORMAL UNIVERSITY
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