A class of triphenyldioxazinimide diploid compound and preparation method thereof

A technology of triphenyl dioxazine imide and monobromotriphenyl dioxazine imide, which is applied in the field of triphenyl dioxazine imide diploid compound and preparation thereof, and can solve the problem of limiting the application and development of dyes , poor solubility, unfavorable solution processing and other problems, to achieve the effect of excellent electron transport performance and good redox characteristics

Inactive Publication Date: 2020-07-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor solubility of triphenyldioxazine dyes is not conducive to solution processing, and the dye molecules have strong π-π conjugation, and molecular aggregation is prone to occur in the solid state, which greatly limits the application and development of such dyes

Method used

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  • A class of triphenyldioxazinimide diploid compound and preparation method thereof
  • A class of triphenyldioxazinimide diploid compound and preparation method thereof
  • A class of triphenyldioxazinimide diploid compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Monobromotriphenyldioxazinimide (2.00mmol), bistributyltinthiophene (1.00mmol) and Pd 2 (dba) 3 (0.1 mmol) was added into the reactor, and toluene was used as a solvent, and the reaction was heated at 80° C. for 12 h. The end point of the reaction was determined by thin-plate chromatography, and the reaction was stopped. Liquid dichloromethane and water, washed with water, dried, desolvated, and purified by silica gel column chromatography to obtain a purple solid, yield: 72%, HRMS: 2049.3177 (m / z).

Embodiment 2

[0033]

[0034] Monobromotriphenyldioxazinimide (5.00mmol), bistributyltindithiophene (1.00mmol) and Pd 2 (dba) 3 (0.2 mmol) was added into the reactor, chlorobenzene was used as a solvent, and the reaction was heated at 100° C. for 16 h. The end point of the reaction was determined by thin-plate chromatography, and the reaction was stopped. Liquid dichloromethane and water, washed with water, dried, desolvated, and purified by silica gel column chromatography to obtain a purple solid, yield: 78%, HRMS: 1966.9487 (m / z).

Embodiment 3

[0036]

[0037] Monobromotriphenyldioxazinimide (3.00mmol), bisborate triphenylamine (1.00mmol), Pd(PPh 3 ) 4 (0.05mmol), 2M K 2 CO 3 An aqueous solution (4.00 mmol) was added into the reactor, ethylene glycol monomethyl ether was used as a solvent, and the reaction was heated at 120° C. for 8 hours. The end point of the reaction was determined by thin-plate chromatography, and the reaction was stopped. Liquid dichloromethane and water, washed with water, dried, desolvated, and purified by silica gel column chromatography to obtain a purple solid, yield: 82%, HRMS: 2162.1345 (m / z).

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PUM

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Abstract

The invention discloses a triphenyldioxinimide diploid compound and a preparation method thereof, and belongs to the technical field of organic synthesis. A triphenyldioxinmide diploid is synthesizedand obtained by adopting monobromotriphenyldioxinimide and reacting with a monoboric acid aromatic hydrocarbon, a monopinacol borate aromatic hydrocarbon or a monotributyltin aromatic hydrocarbon under the action of a catalyst and an alkali through a C-C coupling method. Through the introduction of an aliphatic side chain of the triphenyldioxazine imide diploid, the dissoluvability of the triphenyldioxinimide diploid is effectively ameliorated; a conjugately bridged diploid structure can generate spatial warping to inhibit molecular aggregation and the triphenyldioxinimide diploid compound canshow excellent photoelectric performance when being applied to an organic photoelectric device.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a class of triphenyldioxazine imide diploid compounds and a preparation method thereof. Background technique [0002] In recent years, ladder-shaped conjugated molecules containing imide structures have attracted extensive attention from researchers in the field of optoelectronics. Ladder-shaped conjugated imide derivatives have good visible light absorption and electron transport properties. As organic electron transport materials, they can be applied to organic thin film solar cells, organic field effect transistors, organic electroluminescent diodes and organic lasers. In 2008, our research group chemically modified the classic triphenyldioxazine dye, and the synthesized triphenyldioxazine derivatives were used as electron transport materials, and the organic field effect transistor produced by vacuum evaporation has a high Electron mobility and good stability. However, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/00
Inventor 肖义王赫麟陈令成
Owner DALIAN UNIV OF TECH
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