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The preparation method of octafluoro substituted phthalocyanine

A technology for octafluoro-substituted phthalocyanines, which is applied in the field of preparation of octafluoro-substituted phthalocyanines, can solve the problems of few synthesis methods of octafluoro-substituted phthalocyanines, and achieve the effects of low raw material cost, high yield, and simple post-treatment

Active Publication Date: 2016-09-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, in the literature (J.Mater.Chem., 1998,8,945-954.J.Porphyrins Phthalocyanines2005,9:626-636) reports more is the preparation of perfluorinated phthalocyanine compounds, for octafluoro substituted phthalocyanines There are few synthetic methods for compounds

Method used

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  • The preparation method of octafluoro substituted phthalocyanine
  • The preparation method of octafluoro substituted phthalocyanine
  • The preparation method of octafluoro substituted phthalocyanine

Examples

Experimental program
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Effect test

Embodiment 1

[0036](1) Preparation of 4,5-dichlorophthalic anhydride: weigh 4,5-dichlorophthalic acid (10.15g, 43mmol) into a 50ml four-necked flask, then add acetic anhydride (30ml, 294mmol), Stir magnetically, heat, and raise the temperature to 110°C to dissolve all the solids, continue to heat up to 140°C, react for 1 hour, spot plate detection, the raw materials are completely reacted, stop the reaction. After cooling and standing to room temperature, a large amount of white flaky crystals precipitated, filtered, the filter cake was washed three times with petroleum ether, and vacuum-dried to obtain 9.69 g of white flaky crystals and white powder solids. The purity measured by high performance liquid chromatography was 99.9%. Efficiency: 95.09% (literature value 93%), melting point: 185-187°C (literature value 185-187°C).

[0037] (2) Synthesis of N-phenyl-4,5-dichlorophthalimide: Take 4,5-dichlorophthalic anhydride (5g, 0.023mol), aniline 2.80ml, anhydrous ice Add 40ml of acetic acid...

Embodiment 2

[0046] (1) Preparation of 4,5-dichlorophthalic anhydride: Add acetic anhydride (13ml, 125mmol) and react for 2.5h to obtain 8.90g of white flaky crystals and white powder. Other conditions and parameters are the same as those in the first embodiment.

[0047] (2) Synthesis of N-phenyl-4,5-dichlorophthalimide: take 4,5-dichlorophthalic anhydride (5g, 0.023mol), aniline 9.0ml, anhydrous ice Add 50ml of acetic acid into a 100ml four-necked flask in turn, stir magnetically, heat to reflux to 100°C, and react for 5h to obtain 5.32g of the product. Other conditions and parameters are the same as those in the first embodiment.

[0048] (3) Synthesis of N-phenyl-4,5-difluorophthalimide: put dry sodium fluoride (1.47g, 35mmol) into a dry four-neck flask, add redistilled N, N-dimethylformamide 10ml, magnetic stirring, heating up to 150°C, then adding dry N-phenyl-4,5-dichlorophthalimide (1.00g, 3.4mmol) in sequence, phase transfer Catalyst tetrabutylammonium bromide (0.02g, 0.06mmol)...

Embodiment 3

[0052] (1) Preparation of 4,5-dichlorophthalic anhydride: add acetic anhydride (85ml, 125mmol) and react for 4h to obtain 9.12g of white flaky crystals and white powder. Other conditions and parameters are the same as those in the first embodiment.

[0053] (2) Synthesis of N-phenyl-4,5-dichlorophthalimide: Take 4,5-dichlorophthalic anhydride (5g, 0.023mol), distill 20ml of aniline newly, Add 40ml of water and glacial acetic acid to a 100ml four-necked flask in sequence, stir magnetically, heat to 120°C, react for 10h, stop the reaction, and obtain 4.89g of the product. Other conditions and parameters are the same as those in the first embodiment.

[0054] (3) Synthesis of N-phenyl-4,5-difluorophthalimide: put dry cesium fluoride (2.97g, 30mmol) into a four-neck flask, add 20ml of dimethyl sulfoxide , magnetically stirred, heated up to 150°C, then added dry N-phenyl-4,5-dichlorophthalimide (2.00g, 7mmol), phase transfer catalyst polyethylene glycol-6000 (0.12 g, 0.02mmol) w...

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Abstract

The invention relates to a method for preparing octafluoro-substituted phthalocyanine. According to the method, easily available 4,5-dichlorophthalic acid serving as a raw material is subjected to five-step reactions, namely acetic anhydride dehydration, aniline imidization, potassium fluoride fluorination, hydrolysis and one-step condensation to obtain a target product, namely an octafluoro-substituted phthalocyanine compound. The method has the advantages of low raw material cost, mild reaction condition, safe experiment operation, simple post-treatment, relatively high target product yield, high purity and the like. A novel method is provided to preparation for synthesizing octafluoro-substituted phthalocyanine compounds, synthesis researches of octafluoro-substituted phthalocyanine compounds are promoted, and more possibility is provided to application of the octafluoro-substituted phthalocyanine compounds serving as semiconductor materials in researches of dye-sensitized solar cells, organic thin-film transistors and other aspects. The method can be easily industrialized, and the obtained product has high purity and stable quality.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry, and in particular relates to a preparation method of octafluoro-substituted phthalocyanine. Background technique [0002] Phthalocyanine molecules are a class of macrocyclic compounds with 18π conjugated electrons. They have excellent photophysical and photochemical properties. Phthalocyanines with substituted ligands. Phthalocyanine rings can coordinate with almost all metal elements in the periodic table, and new materials with different optical properties can be obtained. Phthalocyanine compounds are used in a series of fields such as nonlinear optical materials, light confinement materials, electronic components, electrochromic display materials, liquid crystal display materials, photodynamic therapy drugs, near-infrared electroluminescent devices, organic semiconductor materials and solar cells. with broadly application foreground. [0003] The phthalocyanine intermediate N-phenyl-4,5-d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 王世荣邵小娜肖殷李祥高
Owner TIANJIN UNIV
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