Justin Kahle , Niklas J. Hermann , Martin C. Dietl , Patrick D. Römgens , Kim J. Warth , Christopher Hüßler , Alexandra V. Mackenroth , Fabian Baier , Ute Zschieschang , Petra Krämer , Frank Rominger , Matthias Rudolph , Hagen Klauk , Jana Zaumseil , A. Stephen K. Hashmi
{"title":"π-Extended dipyrrolopyrazines as multifunctional materials","authors":"Justin Kahle , Niklas J. Hermann , Martin C. Dietl , Patrick D. Römgens , Kim J. Warth , Christopher Hüßler , Alexandra V. Mackenroth , Fabian Baier , Ute Zschieschang , Petra Krämer , Frank Rominger , Matthias Rudolph , Hagen Klauk , Jana Zaumseil , A. Stephen K. Hashmi","doi":"10.1039/d6qo00350h","DOIUrl":null,"url":null,"abstract":"<div><div>Here, we report a convergent synthetic strategy employing a gold-catalyzed cyclization to construct novel π-extended dipyrrolopyrazine () derivatives in a modular fashion. The robust design of <strong>s</strong> ensures high thermal stability, excellent oxidation resistance, and adaptability for integration into organic thin-film transistors and photoluminescent devices. Systematic exploration of substitution patterns revealed insights into structure–property relationships, particularly the influence of isosteric CH/N exchange. These findings establish <strong>s</strong> as a versatile platform for multifunctional materials, offering pathways for innovations in organic electronics.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"13 12","pages":"Pages 3717-3727"},"PeriodicalIF":0.0000,"publicationDate":"2026-06-16","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/S205241292600210X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/4/27 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Here, we report a convergent synthetic strategy employing a gold-catalyzed cyclization to construct novel π-extended dipyrrolopyrazine () derivatives in a modular fashion. The robust design of s ensures high thermal stability, excellent oxidation resistance, and adaptability for integration into organic thin-film transistors and photoluminescent devices. Systematic exploration of substitution patterns revealed insights into structure–property relationships, particularly the influence of isosteric CH/N exchange. These findings establish s as a versatile platform for multifunctional materials, offering pathways for innovations in organic electronics.