Sven M. Elbert , Evelin Bolgert , Owen T. A. Paine , Farhad Ghalami , Wen-Shan Zhang , Ute Zschieschang , Frank Rominger , Dennis Popp , Hagen Klauk , Marcus Elstner , Michael Mastalerz
{"title":"Z-shaped polycyclic aromatic hydrocarbons with embedded five-membered rings and their application in organic thin-film transistors†‡","authors":"Sven M. Elbert , Evelin Bolgert , Owen T. A. Paine , Farhad Ghalami , Wen-Shan Zhang , Ute Zschieschang , Frank Rominger , Dennis Popp , Hagen Klauk , Marcus Elstner , Michael Mastalerz","doi":"10.1039/d4qo01252f","DOIUrl":null,"url":null,"abstract":"<div><div>Z-shaped polycyclic hydrocarbons with embedded five-membered rings as well as their diaza-analogues have been synthesized. Soluble congeners were obtained by the introduction of mesityl substituents and studied by cyclo- as well as differential pulse voltammetry revealing an amphoteric redox behavior. Unsubstituted congeners showed close π-stacking in single crystal X-ray diffraction analyses and thus promising characteristics for the application as semiconducting materials in p-channel thin-film transistors (TFTs). The hole transport characteristics of the corresponding devices were investigated by GIWAXS.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 19","pages":"Pages 5340-5349"},"PeriodicalIF":0.0000,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S205241292400562X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/7/30 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Z-shaped polycyclic hydrocarbons with embedded five-membered rings as well as their diaza-analogues have been synthesized. Soluble congeners were obtained by the introduction of mesityl substituents and studied by cyclo- as well as differential pulse voltammetry revealing an amphoteric redox behavior. Unsubstituted congeners showed close π-stacking in single crystal X-ray diffraction analyses and thus promising characteristics for the application as semiconducting materials in p-channel thin-film transistors (TFTs). The hole transport characteristics of the corresponding devices were investigated by GIWAXS.
我们合成了内嵌五元环的 Z 型多环烃及其重氮类似物。通过引入间苯二酚取代基获得了可溶性同系物,并通过环伏安法和差分脉冲伏安法进行了研究,结果显示了两性氧化还原行为。未取代的同系物在单晶 X 射线衍射分析中显示出紧密的 π 堆积,因此具有在 p 沟道薄膜晶体管(TFT)中用作半导体材料的良好特性。通过 GIWAXS 研究了相应器件的空穴传输特性。