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Tetra-substituted phenoxyl zinc phthalocyanine and preparation method thereof

A phenoxyzinc and four-substituted technology, which is applied in the field of synthesis of organic and metal coordination compounds, can solve the problems of retarded phthalocyanine application, easy agglomeration, low conversion efficiency, etc., achieve unique light and electricity, and increase solubility , the effect of increasing the distance between molecules

Inactive Publication Date: 2016-09-28
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional phthalocyanines have low solubility in organic solvents, are prone to agglomeration, and have defec

Method used

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  • Tetra-substituted phenoxyl zinc phthalocyanine and preparation method thereof
  • Tetra-substituted phenoxyl zinc phthalocyanine and preparation method thereof
  • Tetra-substituted phenoxyl zinc phthalocyanine and preparation method thereof

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preparation example Construction

[0017] The reaction mechanism of the preparation method of the described four-substituted phenoxy zinc phthalocyanine is as follows:

[0018] (1) Basic catalyst K 2 CO 3 , Reaction of hydroquinone and 4-nitrophthalonitrile in a molar ratio of 1 to 2:1.9 to 2.1:1 to obtain 4-hydroxyphenoxyphthalonitrile;

[0019]

[0020] (2) Basic catalyst K 2 CO 3 , 4-hydroxyphenoxy phthalonitrile and 1-bromooctane in a molar ratio of 1 to 3:1:1 to 5 react to obtain 4-(p-octyloxyphenoxy) phthalonitrile;

[0021]

[0022] (3) DBU, 4-(p-octyloxyphenoxy) phthalonitrile and zinc acetate react in a molar ratio of 1 to 4:4:1 to 2 to prepare tetrasubstituted phenoxy zinc phthalocyanine;

[0023]

[0024] In the formula,

[0025] In the aforementioned preparation method, DBU is 1,8-diazabibicyclo[5.4.0]undec-7-ene.

[0026] The reaction route of the zinc phthalocyanine preparation method is shown in the following formula.

[0027]

[0028]

Embodiment 1

[0030] (1) Purification of DMF (N,N-dimethylformamide): 150ml DMF of analytical grade and 4g CaH 2 Place in a single-necked flask, seal it, then heat and reflux at 130°C for 12h, and after cooling to room temperature, distill the solution under reduced pressure, take a fraction at 80°C, and place the obtained fraction together with 4A molecular sieves in a clean and dry Erlenmeyer flask for sealed storage.

[0031] (2) Preparation of 4-hydroxyphenoxyphthalonitrile: add hydroquinone (9.6097g, 87.27mmol), potassium carbonate (6.0085g, 43.54mmol) and 50ml of anhydrous DMF in a three-necked flask, nitrogen protection , reacted at 25° C. for 1 h, and then added 4-nitrophthalonitrile (7.5318 g, 43.54 mmol) to continue the reaction for 24 h. Pour into 500ml of 0.1mol / L dilute hydrochloric acid after the reaction. Suction filtration under reduced pressure, then wash the filter cake with distilled water until the filtrate Ph=7, dry the filter cake, and then recrystallize in a mixed so...

Embodiment 2

[0036] (1) Refining of DMF: 150ml DMF of analytical grade and 4g CaH 2 Place in a single-necked flask, seal it, then heat and reflux at 130°C for 12h, and after cooling to room temperature, distill the solution under reduced pressure, take a fraction at 80°C, and place the obtained fraction together with 4A molecular sieves in a clean and dry Erlenmeyer flask for sealed storage.

[0037] (2) Preparation of 4-hydroxyphenoxyphthalonitrile: add hydroquinone (4.8048g, 43.68mmol), potassium carbonate (6.0182g, 43.60mmol) and 50ml of anhydrous DMF in a three-necked flask, nitrogen protection , reacted at 25° C. for 1 h, and then added 4-nitrophthalonitrile (7.5426 g, 43.60 mmol) to continue the reaction for 24 h. Pour into 500ml of 0.1mol / L dilute hydrochloric acid after the reaction. Suction filtration under reduced pressure, then wash the filter cake with distilled water until the filtrate Ph=7, dry the filter cake, and then recrystallize in a mixed solution of absolute ethanol a...

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Abstract

The invention provides tetra-substituted phenoxyl zinc phthalocyanine which has a chemical structural formula as shown in the specification. Novel tetra-substituted phenoxyl zinc phthalocyanine which is not reported can be synthesized by introducing phenoxyl with an alcoxyl long chain to the periphery of zinc phthalocyanine macrocycle for the first time. Compared with short chain phenoxyl in previous reports, an octyloxy chain containing eight carbon atoms is introduced into the tetra-substituted phenoxyl zinc phthalocyanine, the solubility of the compound in an organic solvent can be greatly improved due to introduction of the flexible chain octyloxy, and the tetra-substituted phenoxyl zinc phthalocyanine has the advantages of mild reaction conditions, safe experiment operation, simple post-treatment, high target product yield and the like.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, in particular to a novel tetrasubstituted phenoxy zinc phthalocyanine 2(3), 9(10), 16(17), 23(24)-tetrakis-(p-octyl Oxyphenoxy) zinc phthalocyanine, and its preparation method and application. Background technique [0002] Dye-sensitized solar cell (DSSC) is a low-cost, high-efficiency and environmentally friendly solar cell. Since its birth in the 1990s, it has been highly valued by researchers in many countries and has shown very attractive application prospects. . In the DSSC system, the nanoporous semiconductor electrode adsorbed with a single layer of photosensitizing dye is the core part. The photosensitizing dye plays the role of absorbing solar energy and injecting excited state electrons into the conduction band of nano-semiconductor, which is one of the decisive factors for DSSC to obtain high photoelectric conversion efficiency and long life. [0...

Claims

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Application Information

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IPC IPC(8): C07D487/22H01G9/20
CPCC07D487/22H01G9/2059Y02E10/542
Inventor 于晓燕刘家余胡红鑫张庆新
Owner HEBEI UNIV OF TECH