Truxeneone-benzophenanthrene disk-shaped liquid crystal compound and preparation method thereof

Abstract

The invention relates to a truxeneone-benzophenanthrene disk-shaped liquid crystal organic semiconductor material and a preparation method thereof. The method includes adding monobromobenzophenanthrene and potassium carbonate into N, N'-dimethylformamide, adding a trihydroxytruxene compound under the protection of inert gases, heating to the temperature of 80 DEG C to conduct a reaction for 36-48hours while stirring, removing the gas protection, and exposing the reaction system in the air to continue heating for 24-36 hours of reaction; after the reaction is completed, cooling reaction liquidto room temperature, pouring the reaction liquid into ice water to precipitate out red solids, performing suction filtration to obtain a crude product, performing vacuum drying, purifying the crude product through column chromatography isolation, taking dichloromethane as eluent, and recrystallizing a mixed organic solvent, and performing vacuum drying. The synthesis method has the advantages ofsimple operation, mild reaction condition and moderate yield, and the reactions of etherification-based polymer construction and oxidation-based truxeneone acquisition are connected in series by one step, and the p-n type disk-shaped liquid crystal compound is successively synthesized; the efficient preparation method is provided for complex truxeneone derivatives.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic functional materials, and in particular relates to a tuxylenone-triphenylene discotic liquid crystal organic semiconductor material and a preparation method thereof. The molecular structure of this type of material is as follows: [0002] Background technique [0003] As a new member of organic semiconductor materials, discotic liquid crystal semiconductors have unique properties such as self-assembly order, self-repairing of structural defects, and high anisotropic charge mobility. The application and development of discotic liquid crystal semiconductors in fields such as organic field-effect transistors and organic solar cells are attracting increasing attention from researchers. Discotic liquid crystal polymers have a definite molecular weight like unimolecular compounds, and are different from unimolecular compounds. They tend to have film-forming properties and glassy struct...

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Problems solved by technology

Pei Jian et al. used 3,8,13-trihydroxytoxyne and alkyl bromide to generate ether when heated to 100°C in air under the condition of potassium carbonate as base and N,N'-dimethylformamide as solvent. 3,8,13-tri(n-hexyloxy)toxynone was prepared by one-step tandem reaction of oxidation and oxidation, but the yield was only 36%; in addition, they also tried to use a two-step reaction method, first trihydroxytoxyne and bromine Under the conditions of potassium carbonate as alkali and ethanol as solvent, etherification reaction occurs when heating to 100°C in air to generate 3,8,13-tri(n-hexyloxy)tuxene with a yield of 51%. Methylammonium hydroxide was used as the base and tetrahydrofuran was used as the solvent, and the oxidation reaction occurred under reflux in an oxygen atmosphere to obtain 3,8,13-tri(n-hexyloxy)toxynone【Wang, J.Y.; Yan, J.; Ding, L.; Ma, Y. G.; Pei, J. Adv. Funct. Mater ., 2009, 19, 1746–1752.]

In summary, the existing synthetic methods for preparing and synthesizing tuxylenone derivatives are not efficient, especially for the synthesis of more complex tuxylenone derivatives, which need further research

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