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Pyrrole-containing triphenylamine conjugated schiff base compound, and preparation method and application thereof

A technology of pyrrolyltriphenylamine and Schiff base, applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve the problems of high synthesis cost and complex synthesis method, and achieve the effect of high degree of conjugation

Inactive Publication Date: 2015-07-22
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to solve the problems of complex synthesis methods and high synthesis costs of existing organic electrochromic materials, and provide a kind of pyrrolyl triphenylamine conjugated Schiff base compound and its preparation method and application

Method used

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  • Pyrrole-containing triphenylamine conjugated schiff base compound, and preparation method and application thereof
  • Pyrrole-containing triphenylamine conjugated schiff base compound, and preparation method and application thereof
  • Pyrrole-containing triphenylamine conjugated schiff base compound, and preparation method and application thereof

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specific Embodiment approach 1

[0042] Specific implementation mode 1: This implementation mode is a kind of pyrrolyltriphenylamine-containing conjugated Schiff base compound whose structural formula is as follows:

[0043] where the R 1 For H, R 2 for H; R 1 for when R 2 for H, -CH 3 or -OCH 2 CH 3 .

[0044] The beneficial effect of this implementation mode:

[0045]1. The Schiff base compound of the present embodiment changes the shortcomings of narrow application range and single function of Schiff base in the past, and provides a multifunctional Schiff base; a -C=N- double bond structure is formed in the molecule, and the double bond connects benzene Ring and pyrrole, forming a large conjugated structure, so that the electron cloud can be transported in a very long molecular chain, prone to light absorption, resulting in a color change after protonation in acid or oxidation with an applied voltage, and this change is reversible , accompanied by a reversible color change;

[0046] 2. In th...

specific Embodiment approach 2

[0047] Specific embodiment two: This embodiment is a preparation method of a conjugated Schiff base compound containing pyrrolyl triphenylamine, which is prepared according to the following method:

[0048] 1. Mix the triphenylamine derivative and absolute ethanol, and then magnetically stir for 10 minutes to 15 minutes at a temperature of 79°C to 80°C and a stirring speed of 200r / min to 300r / min to obtain an ethanol solution of the triphenylamine derivative;

[0049] The volume ratio of the mass of the triphenylamine derivative described in step 1 to absolute ethanol is 0.1g: (10mL~20mL);

[0050] 2. Under a nitrogen atmosphere, add pyrrole-2-carbaldehyde ethanol solution dropwise to triphenylamine derivative ethanol solution at a rate of 20 drops / min to 30 drops / min, and then react at a temperature of 79°C to 80°C 20h~24h, get the reactant;

[0051] The volume ratio of the mass of pyrrole-2-carbaldehyde in the pyrrole-2-carbaldehyde ethanol solution described in step 2 to a...

specific Embodiment approach 3

[0057] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the triphenylamine derivative described in step one is Others are the same as in the second embodiment.

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Abstract

The invention relates to a compound, and a preparation method and application thereof, in particular to a pyrrole-containing triphenylamine conjugated schiff base compound, and a preparation method and application thereof, and aims to solve the problem that the conventional organic electrochromic material is complex in synthetic method and high in synthetic cost. The structural formula of the pyrrole-containing triphenylamine conjugated schiff base compound is shown in the specification. The preparation method comprises the following steps: firstly, preparing a triphenylamine derivative ethanol solution; secondly, dropwise adding a pyrrole-2-carboxaldehyde ethanol solution in the triphenylamine derivative ethanol solution to obtain a reactant; thirdly, adding the reactant in a small polar organic solvent to precipitate to obtain a product I, performing suction filtration on the product I n to obtain a product II, purifying the product II by an Al2O3 chromatographic column to obtain a product III, and drying the product III. The pyrrole-containing triphenylamine conjugated schiff base compound is taken as an off-color material to be applied in electrochromic display material, acidichromism display material, acid sensing material, hole-transport material or anti-counterfeit material and camouflage material. The pyrrole-containing triphenylamine conjugated schiff base compound can be obtained.

Description

technical field [0001] The present invention relates to a kind of compound and preparation method and application. Background technique [0002] With the continuous development of society and continuous progress of human beings, people's requirements for materials are also gradually increasing. Color-changing materials are new functional materials developed on the basis of this requirement. Color-changing materials refer to materials that can change color when external conditions change. This material is widely used in electronics, energy, construction, etc. Electrochromic materials are the focus of research. They have attracted much attention in the past two decades and have great application prospects and commercial value. The synthesis of existing organic electrochromic materials requires expensive raw materials and harsh synthesis conditions, which limit the scope of application. Contents of the invention [0003] The purpose of the present invention is to solve the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34C09K9/02
CPCC07D207/335C07D207/34C09K9/02C09K2211/1007C09K2211/1014C09K2211/1029
Inventor 牛海军李宇田甜宋文琪蔡姝崴
Owner HEILONGJIANG UNIV
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