Fang Sun, Yangqifu Cui, Zhenbo Zhao, Lingcheng Chen, Yi Xiao
{"title":"Triphenodioxazine Diimides: Design, Synthesis, and Properties.","authors":"Fang Sun, Yangqifu Cui, Zhenbo Zhao, Lingcheng Chen, Yi Xiao","doi":"10.1021/acs.orglett.4c02731","DOIUrl":null,"url":null,"abstract":"<p><p>To increase solubility and decrease the lowest unoccupied molecular orbital (LUMO) energy levels of triphenodioxazine (<b>TPDO</b>), a novel series of imide-fused <b>TPDO</b> derivatives (<b>TPDODIs</b>) were designed, synthesized, and investigated. The introduction of alkyl diimide groups endows <b>TPDODIs</b> with high solubility and LUMO energy levels below -3.90 eV. <b>TPDODIs</b> also show strong absorption in the visible region with high maximum molar extinction coefficients and high fluorescence quantum yields (0.67 and 0.71, respectively). Moreover, <b>TPDODIs</b> display thermotropic liquid-crystalline behavior as indicated by spindly nematic or dendritic textures. Their high solubility and low LUMO levels suggest these materials are well-suited for solution-processable n-type electronic devices.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"7875-7879"},"PeriodicalIF":5.0000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c02731","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/5 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
To increase solubility and decrease the lowest unoccupied molecular orbital (LUMO) energy levels of triphenodioxazine (TPDO), a novel series of imide-fused TPDO derivatives (TPDODIs) were designed, synthesized, and investigated. The introduction of alkyl diimide groups endows TPDODIs with high solubility and LUMO energy levels below -3.90 eV. TPDODIs also show strong absorption in the visible region with high maximum molar extinction coefficients and high fluorescence quantum yields (0.67 and 0.71, respectively). Moreover, TPDODIs display thermotropic liquid-crystalline behavior as indicated by spindly nematic or dendritic textures. Their high solubility and low LUMO levels suggest these materials are well-suited for solution-processable n-type electronic devices.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
