Carbazolyl-containing isoindigo polymer and its preparation method and application in electrochromism

An electrochromic layer and electrochromic device technology are applied to carbazole group-containing isoindigo polymers and their preparation and application in electrochromism, and can solve the problem of narrow application range of isoindigo and low solubility of isoindigo And other issues

Inactive Publication Date: 2018-10-12
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problem that the application range of isoindigo is narrow due to the low solubility of isoindigo in organic solvents, the present invention proposes a carbazole-based isoindigo polymer and its preparation method and application in electrochromism

Method used

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  • Carbazolyl-containing isoindigo polymer and its preparation method and application in electrochromism
  • Carbazolyl-containing isoindigo polymer and its preparation method and application in electrochromism
  • Carbazolyl-containing isoindigo polymer and its preparation method and application in electrochromism

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specific Embodiment approach 1

[0086] Embodiment 1: The structural formula of the carbazolyl-containing isoindigo polymer in this embodiment is:

[0087] where n is a positive integer.

[0088] This embodiment has the following beneficial effects:

[0089] The isoindigo conjugated polymer containing carbazole groups and isoindigo groups in this embodiment increases the solubility of isoindigo due to the introduction of a long alkyl chain, and is easily soluble in polar solvents. Every 10 ml of polar solution 1~1.5g soluble in medium; slightly soluble in non-polar solvent, 0.1~0.2g per 10ml polar solution;

[0090] 2. The polymer of this embodiment has excellent electrochromic properties and memory properties, and can be applied in the field of electrochromism, and it also has good performance in explosive detection and photoelectric detection;

[0091] Electrochromism refers to the phenomenon of color change caused by electrochemical redox reaction of substances under the driving of external voltage or ...

specific Embodiment approach 2

[0094] Specific embodiment 2: The preparation method of the carbazole group-containing isoindigo polymer of the present embodiment is carried out according to the following steps:

[0095]1. Synthesis of N-(4-(9H-carbazol-9-yl)phenyl)-4-bromo-N-(4-bromophenyl)aniline monomer:

[0096] ①, in N 2 Under the atmosphere, place carbazole monomer, sodium hydride and anhydrous N,N-dimethylformamide in a three-necked flask, add p-fluoronitrobenzene at a rate of 1 to 2 drops per second while stirring, and heat up to After 114~115 ℃, carry out isothermal reaction, use thin layer chromatography to judge whether the isothermal reaction is over, and cool down after the isothermal reaction is over; place the reaction product in cold water until the crude product is precipitated, then filter out the crude product, and wash the crude product with hot water 2 to 3 times, use ethanol to recrystallize the crude product washed with hot water, filter out the crystalline product after recrystalliza...

specific Embodiment approach 3

[0149] Embodiment 3: The difference between this embodiment and Embodiment 2 is that the eluent used in the separation of solid products by the chromatographic column described in step 2 (2) is a mixture of dichloromethane and petroleum ether, and dichloromethane and The volume ratio of petroleum ether is 1:(7~8). Other steps and parameters are the same as in the second embodiment.

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Abstract

The invention discloses a carbazolyl-containing isoindigo polymer and its preparation method and application in electrochromism and relates to an isoindigo polymer and a preparation method and application thereof. The carbazolyl-containing isoindigo polymer solves the problem that the low solubility of isoindigo in an organic solvent causes a narrow isoindigo application range. The carbazolyl-containing isoindigo polymer has a structural formula shown in the description. In the formula, n represents a positive integer. The preparation method comprises: 1, synthesizing an N-(4-(9H-carbazolyl-9-yl)phenyl)-4-bromo-N-(4-bromophenyl)aniline monomer, 2, preparing isoindigo derivatives, and 3, preparing the carbazolyl-containing isoindigo polymer. The carbazolyl-containing isoindigo polymer is used as an electrochromic layer in an electrochromic device for electrochromism. The polymer has excellent electrochromic properties and memory properties, can be applied to the field of electrochromism, and has excellent performances in explosive detection and photodetection. The invention provides the preparation method and application of the isoindigo polymer.

Description

technical field [0001] The invention relates to an isoindigo polymer, a preparation method and application thereof. Background technique [0002] Isoindigo is an isomer of indigo. The isoindigo unit has two strong electron-withdrawing lactam groups, and there are multiple positions where functional groups can be introduced, so compounds with various properties can be obtained. Isoindigo has a large local dipole moment, so it can effectively enhance the intra-molecular and intermolecular interactions, and it can be easily and efficiently introduced into the alkyl chain to bring good solubility and other advantages. [0003] However, in general methanol, ethanol, N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, chlorobenzene and other organic solvents, the solubility of isoindigo is generally insoluble or insoluble. Therefore, isoindigo is difficult to process into a film, and isoindigo can only be used in the fields of organic photovoltaics (OPV), solar cells...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/124C08G2261/124C08G2261/1412C08G2261/143C08G2261/18C08G2261/3162C08G2261/3241C08G2261/414C08G2261/512C08G2261/522C08G2261/54C08G2261/592C08G2261/64C08G2261/94
Inventor 牛海军路庆义赵硕杨彩誉张旭葛浩然范景贺
Owner HEILONGJIANG UNIV
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