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Effect of halogenated substituent on the properties of aza-octacenes

机译:卤代取代基对AZA-Octacenes性质的影响

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摘要

We systematically designed and developed three novel halogenated aza-octacene derivatives, which have the same π-conjugated backbone with different terminal halogen groups (F, Cl, Br). These aza-octacene derivatives are synthesized by acid-catalyzed condensation of naphthalene-bisisatin with 4,5-dihalo-l,2-phenylenediamine. The in-depth experimental and theoretical analyses on these molecules, using the non-halogenated system as a reference, allowed us to understand the impact of halogenation on electronic and optical properties. Both electronic affinity (EA) and ionization potential (IP) are increased through peripheral halogen substitution. Chlorination enhances the EA more effectively compared with fluorination and bromination. Micro-crystal devices based on the bromine substituted aza-octacene derivative show only p-type charge transport behavior. In contrast, the chlorinated and the fluorinated aza-octacene derivatives exhibit ambipolar charge transport.
机译:我们系统地设计和开发了三种新的卤代芳基 - 辛酸衍生物,其具有与不同末端卤素基团(F,Cl,Br)相同的π-共轭骨架。这些AZA-辛酸衍生物通过酸催化的萘 - 双鉴蛋白缩合合成,用4,5-二卤胺-1,2-苯二胺。使用非卤化系统作为参考的这些分子对这些分子的深度实验和理论分析使我们能够了解卤化对电子和光学性质的影响。通过外周卤素取代增加,电子亲和力(EA)和电离电位(IP)都增加。氯化与氟化和溴化相比更有效地增强了EA。基于溴取代的AZA-八元烯衍生物的微晶装置仅显示P型电荷传输行为。相反,氯化和氟化阿扎 - 辛酸衍生物表现出非胆电荷输送。

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  • 来源
    《Organic Electronics》 |2020年第10期|105895.1-105895.5|共5页
  • 作者单位

    College of Chemistry and Chemical Engineering University of South China Hengyang hunan China Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education School of Materials Science and Engineering Sun Yat-Sen University Guangzhou 510275 China;

    Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education School of Materials Science and Engineering Sun Yat-Sen University Guangzhou 510275 China;

    College of Chemistry and Chemical Engineering Shanghai University of Engineering Science 333 Longteng Road Shanghai 201620 China;

    College of Energy Beijing University of Chemical Technology Beijing 100029 China;

    Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education School of Materials Science and Engineering Sun Yat-Sen University Guangzhou 510275 China;

    Department of Chemistry SRM University - AP Amaravati 522502 India;

    College of Chemistry and Chemical Engineering University of South China Hengyang hunan China;

    Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education School of Materials Science and Engineering Sun Yat-Sen University Guangzhou 510275 China;

    College of Energy Beijing University of Chemical Technology Beijing 100029 China;

    College of Chemistry and Chemical Engineering Shanghai University of Engineering Science 333 Longteng Road Shanghai 201620 China;

    Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education School of Materials Science and Engineering Sun Yat-Sen University Guangzhou 510275 China;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

    Aza-octacenes; Halogenated substituent; Organic crystal transistors;

    机译:AZA-Octacenes;卤化取代基;有机晶体晶体管;

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