A method for the regiospecific synthesis of a class of quinonoid tetraazapentacene organic small molecules

By introducing long alkyl chains and terminal groups into quinone-tetraazapentabenzene compounds through a multi-step synthesis method, the problems of harshness and low solubility of existing synthesis methods have been solved. This has resulted in quinone-tetraazapentabenzene compounds with high solubility and excellent photoelectric properties, thus expanding their application in organic electronic materials.

CN122404341APending Publication Date: 2026-07-17DALIAN UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
DALIAN UNIV OF TECH
Filing Date
2026-04-17
Publication Date
2026-07-17

AI Technical Summary

Technical Problem

Existing methods for synthesizing quinone-tetraazapentabenzene are demanding, have low yields, consume large amounts of solvent, cannot introduce long alkyl chains or modified phenyl groups, and have low solubility, which limits their application in organic electronic materials.

Method used

The reaction was carried out in the presence of N,N-diisopropylethylamine in an alcohol solvent. By combining tin reduction and acidic conditions, a multi-step synthetic method was used to introduce long alkyl chains at the nitrogen position and different groups at the terminal positions to achieve the regiospecific synthesis of quinone-type tetraazapentabenzene.

Benefits of technology

A quinone-type tetraazapentabenzene compound with a long alkyl chain at the nitrogen position and a phenyl side chain was synthesized, which improved the solubility and photoelectric properties, and had a strong absorption peak and a high molar extinction coefficient, making it suitable for organic field-effect transistors and organic solar cells.

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Abstract

本发明公开了一类基于醌式四氮杂五苯有机小分子的区域特异性合成方法。本发明创新性地在四氮杂五苯母核的氮位引入不同的具有侧链的苯基及(含氟)烷基单元,并在端位引入不同的基团,进而实现区域特异性合成。醌式四氮杂五苯已被证明是p型半导体材料,通过引入苯基及(氟代)烷基侧链,实现分子空间扭曲的同时,保留了醌式四氮杂五苯的平面结构,既能提高溶解度,又能抑制分子堆积。另外,此类化合物在可见光区域具有强吸收,具有较高的摩尔消光系数,还具有良好的氧化还原特性和电子传输性能,可作为光电材料,应用于有机电子材料领域。
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