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Method for synthesising tetraphenylporphyrin metal complex via one-step process

A technology of tetraphenylporphyrin and metal complexes, applied in the field of synthetic chemistry, can solve the problems of complex reaction process, long reaction time, difficult operation and the like, and achieves the effects of simple operation, low toxicity of raw materials and time saving.

Active Publication Date: 2015-07-22
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of this method is very low, the first step is only about 15%, the second step is about 80%, and the total yield of the two-step reaction is only about 12%; and the reaction process of this method is complicated, the reaction time is long, and it is not easy to operate

Method used

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  • Method for synthesising tetraphenylporphyrin metal complex via one-step process
  • Method for synthesising tetraphenylporphyrin metal complex via one-step process
  • Method for synthesising tetraphenylporphyrin metal complex via one-step process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1: Since pyrrole is easily oxidized when placed in the air for a long time, first reflux pyrrole at 115°C to obtain a colorless solution and store it in the dark. Measure 0.68ml of pyrrole and pour it into 3.5ml of propionic acid. Shake well and ready to use.

[0030] Step 2: Weigh 2.9g of zinc acetate, dissolve it in 35ml of DMF solution, stir to dissolve it completely, and pour it into a constant pressure dropping funnel for use.

[0031] Step 3: Add 35ml of propionic acid and 1ml of benzaldehyde into a 100ml three-necked flask, stir, and reflux at 140°C. After the temperature is stable, drop in 2.9g of zinc acetate dissolved in 35ml of DMF solution, then slowly add propionic acid solution dissolved in 0.65ml of pyrrole with a rubber dropper, and react for 90min after all the reactants have been added.

[0032] Step 4: After the reaction, cool down, pour the product into about 500ml of water, a large amount of black solid appears, filter with suction, and dry th...

Embodiment 2

[0035] Same as Example 1, but the zinc acetate in the second step changes copper acetate into, and the volume ratio of propionic acid and the DMF solution that is dissolved with copper acetate is 1:1.2, and every gram of copper acetate is dissolved in 15mlDMF solution, and reaction obtains Purple solid powder 0.22g, yield 15%.

Embodiment 3

[0037] Same as Example 1, but the zinc acetate in the second step changes nickel acetate into, and the volume ratio of propionic acid and the solution of the DMF that is dissolved with nickel acetate is 1:1.5, every gram of nickel acetate is dissolved in 16mlDMF solution, reaction Obtained 0.18 g of purple solid powder with a yield of 12%.

[0038] Note: The solubility of copper acetate and nickel acetate in DMF is not very high, and the metal salt should be ground into powder to facilitate dissolution.

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Abstract

The invention discloses a method for synthesising a tetraphenylporphyrin metal complex via a one-step process, comprising the following steps of: (1) dissolving metal acetate in DMF (dimethyl formamide), wherein the ratio of the metal acetate to DMF is 1 g: (8 to 16 ml); (2) adding a solvent, namely, propionic acid, in a reaction container, then sequentially adding benzaldehyde, the DMF solution dissolved with the metal acetate, and a pyrrole solution diluted by propionic acid, and refluxing for 30-120 minutes at a temperature ranging from 120 to 150 DEG C, wherein the molar ratio of benzaldehyde to pyrrole to the metal acetate is 1: 1: (0.25 to 2.5), and the volume ratio of the solvent, namely, propionic acid, to DMF is 1: 1 to 1: 1.5; and (3) after the reaction is concluded, cooling, removing the solvent, and separating to obtain the product. The process has the characteristics of being low in the cost of the used raw materials, moderate in reaction conditions, simple to operate, less in pollution and environment-friendly, changes the previous method of synthesising metalloporphyrin via a two-step process, saves time, and can be used for preparing more tetraphenylporphyrin metal complexes, thus providing more possibility for the applications of various metalloporphyrin dyes to dye-sensitized solar cells.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry, and in particular relates to a synthesis method of a tetraphenylporphyrin metal complex. Background technique [0002] Porphyrin is an important organic compound, which is used to synthesize various pesticides, medicines, advanced dyes and various functional materials. Porphyrins have a macrocyclic conjugated structure with both rigidity and flexibility, certain aromaticity, good stability, and wide spectral response, so they have a wide range of uses. Metalloporphyrin compounds play an important role in medicine, biology, catalysis, materials, etc., which have aroused widespread interest and have great application potential. Tetraphenylporphyrin metal complexes are intermediates of porphyrin-based solar cell sensitizers, which can be used to synthesize porphyrin-based dye sensitizers with more structures, thus providing more opportunities for their application in dye-sensitized solar cells. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22H01G9/20
CPCY02E10/542
Inventor 陈倩倩高洪磊张宪玺杜玉昌
Owner LIAOCHENG UNIV
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