Method for preparing asymmetric 5,15-bis(p-nitrophenyl)-10, 20-diphenyl porphyrin compound

Abstract

The invention relates to a method for preparing an asymmetric 5,15-bis(p-nitrophenyl)-10, 20-diphenyl porphyrin compound. The method comprises the following steps: mixing a nitrobenzene solvent and a C1-C7 straight chain alkyl acid catalyst at the volume ratio of (1 to 21) : 3, preheating at a temperature of 70-145 DEG C, adding substituted benzaldehyde and 5-(4- nitrophenyl) dipyrromethane, subjecting reactants with a concentration of 110-670 mmol/L to a reaction at a temperature of 70-145 DEG C for 20-180 minutes, and separating a reaction mixture through column chromatography to obtain the 5,15-bis(p-nitrophenyl)-10,20-diphenyl asymmetric porphyrin compound of which the maximum yield can reach 32%. Compared with the prior art, the method has the advantages of high yield, simplicity in operation, low cost, resource conservation, easily regulated reaction process, low energy consumption and the like, thereby having a wide application prospect in the industry.

Description

technical field [0001] The invention relates to a preparation method of an asymmetric porphyrin compound. Specifically, it relates to a preparation method of a 5,15-di-p-nitrophenyl-10,20-diphenyl asymmetric porphyrin compound. Background technique [0002] 5,15-di-p-nitrophenyl-10,20-diphenyl asymmetric porphyrins are important intermediates in organic synthesis, widely used in the synthesis of artificial photosynthetic reaction centers, potential anticancer drugs, solar cells, polymerization materials etc. [0003] At present, the preparation methods of 5,15-di-p-nitrophenyl-10,20-diphenyl asymmetric porphyrins mainly include mixed aldehyde method, porphyrin compound nitration method and Macdonald type 2+2 method, etc. [0004] There are two types of Macdonald-type 2+2 methods: two-step one-pot method and one-step method. [0005] Macdonald type 2+2 method (two-step one-pot method): [0006] Rajan Naik et al. (Tetrahedron, 2003.59(13): 2207-2213.) reported a Macdonald-...

AI Technical Summary

Problems solved by technology

[0011] 1. The preparation process is complicated

The reaction needs to be carried out under harsh conditions without oxygen, which leads to high cost and high energy consumption

[0012] 2. The reaction requires the use of expensive and toxic tetrachloro-p-benzoquinone or 2,3-dichloro-5,6-dicyano-p-benzoquinone as an oxidant

Not only the preparation cost is high, but also seriously pollute the environment

[0013] 3. Since the concentration of reactants is not allowed to be too high (less than or equal to 40mmol / L), a large amount of solvent needs to be used, resulting in waste of resources, and the cost of solvent recovery is high, and energy consumption is also high

[0017] 1. Because the concentration of reactants is not allowed to be too high (less than or equal to 53mmol / L), a large amount of solvent needs to be used, resulting in waste of resources, and the cost of solvent recovery is high, and energy consumption is also high

[0018] 2. The reaction medium is single, and its performance is difficult to control

In the reaction, only a single propionic acid is used as the reaction solvent and catalyst, which is not conducive to the regulation of the acidity, polarity, and viscosity of the reaction medium, which is not conducive to the regulation of the reaction.

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