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α-Tetrakis(4-carboxyphenoxy)phthalocyanine and its preparation method and application in the field of molecular self-assembly

A carboxylphenoxy and basephenoxy technology, applied to α-tetra(4-carboxyphenoxy)phthalocyanine and its preparation and application in the field of molecular self-assembly, can solve the problems of low conjugation and the like , to achieve the effects of increased conjugation, good chemical and thermal stability, good solubility and film-forming properties

Inactive Publication Date: 2011-12-14
赵伊博
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention is to solve the technical problem that existing β-tetra(4-carboxyphenoxy) phthalocyanine has low conjugation when self-assembling on the graphite surface, and provides α-tetrakis (4-carboxyphenoxy) phthalocyanine Its preparation method and application in the field of molecular self-assembly

Method used

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  • α-Tetrakis(4-carboxyphenoxy)phthalocyanine and its preparation method and application in the field of molecular self-assembly
  • α-Tetrakis(4-carboxyphenoxy)phthalocyanine and its preparation method and application in the field of molecular self-assembly
  • α-Tetrakis(4-carboxyphenoxy)phthalocyanine and its preparation method and application in the field of molecular self-assembly

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specific Embodiment approach 1

[0010] Specific embodiment one: the structural formula of the α-tetrakis (4-carboxyphenoxy) phthalocyanine of the present embodiment is as follows:

[0011]

[0012] The α-tetrakis (4-carboxyphenoxy) phthalocyanine of the present embodiment has a symmetrical structure, and forms a double-layer assembly structure when self-assembling on the graphite surface. Not only there are large phthalocyanine π-conjugated bonds in the phthalocyanine ring, And there are π-conjugated bonds between the two layers of molecules, which increases the conjugation and has good chemical and thermal stability. α-Tetrakis(4-carboxyphenoxy)phthalocyanine has good solubility and film-forming properties in organic solvents.

specific Embodiment approach 2

[0013] Specific embodiment two: the preparation method of the α-tetra(4-carboxyphenoxy) phthalocyanine of the present embodiment is carried out in the following steps:

[0014] 1. The molar ratio of 3-(4-methoxyphenoxy)phthalonitrile to 1,8-diazabicyclo[5,4,0]undecene-7 is 1:1 ~2,3-(4-methoxyphenoxy)phthalonitrile and n-amyl alcohol in a molar ratio of 1:40~50 Weigh 3-(4-carboxyphenoxy)phthalonitrile Add formonitrile, 1,8-diazabicyclo[5,4,0]undecene-7 and n-amyl alcohol into a reactor with a reflux device, stir and heat to reflux under nitrogen protection, and keep Reflux for 24h to 36h; 2. Remove n-pentanol by distillation under reduced pressure. After cooling to normal temperature, add methanol, stir evenly, let stand for 12h to 24h, then filter, and wash the obtained solid phase with methanol to obtain α-tetra(4- Carbomethoxyphenoxy) phthalocyanine crude product; three, the α-tetrakis (4-methoxyphenoxy) phthalocyanine crude product that step 2 obtains is purified, obtains ...

specific Embodiment approach 3

[0018] Specific embodiment three: the difference between this embodiment and specific embodiment two is that in step one, 3-(4-methoxyphenoxy)phthalonitrile and 1,8-diazabicyclo[5,4 , 0] The molar ratio of undecene-7 is 1:1.1~1.8, and the molar ratio of 3-(4-methoxyphenoxy)phthalonitrile to n-pentanol is 1:41~49. Others are the same as in the second embodiment.

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Abstract

Alpha-tetrakis (4-carboxyphenoxy) phthalocyanine and its preparation method and application in the field of molecular self-assembly relate to a phthalocyanine carboxylic acid derivative and its preparation method and application. The present invention solves the technical problem of low conjugation during self-assembly of the existing β-tetra(4-carboxyphenoxy)phthalocyanine. The structural formula of α-tetra(4-carboxyphenoxy)phthalocyanine is shown in the figure. Method: 3-(4-carbomethoxyphenoxy)phthalonitrile, 1,8-diazabicyclo[5,4,0]undecene-7 and n-pentanol are heated and refluxed for reaction, The crude product of α-tetrakis(4-carbomethoxyphenoxy)phthalocyanine was obtained. After purification, it was dissolved in tetrahydrofuran, reacted with sodium hydroxide and methanol aqueous solution, and then reacted with dilute hydrochloric acid. The precipitated precipitate was filtered and dried. After obtaining α-tetra (4-carboxyphenoxy) phthalocyanine. This product is used for molecular self-assembly. After self-assembly, π-conjugated bonds exist in the phthalocyanine ring and between layers. Can be used in the field of organic field effect transistors.

Description

technical field [0001] The present invention relates to phthalocyanine carboxylic acid derivatives and their preparation method and application. Background technique [0002] Phthalocyanine compounds have good photochemical, photophysical and electronic properties, and are organic compounds with multiple uses, which can be used to construct functional nanostructures and be applied to new molecular devices. Constructing and regulating molecular functional nanostructures is the first step in realizing nanodevices, and it is also the core of constructing molecular devices. By modifying phthalocyanine rings with physical and chemical methods and adjusting their properties, functional materials that can meet various needs can be obtained. The existing β-tetrakis (4-carboxyphenoxy) phthalocyanine forms a single-layer assembly structure when self-assembling on the graphite surface. Only π bonds exist between molecules in the same layer, which has low conjugation and poor film-formi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22H01L51/05
Inventor 赵伊博
Owner 赵伊博
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