{"title":"B←N Lewis Pair-Functionalized Perylenes: Tuning Optoelectronic Properties via Regioisomerization.","authors":"Yufeng Zhang, Junqing Shi, Lei Ji","doi":"10.1021/acs.joc.4c03015","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we report two <i>peri</i>-regioisomers of B←N Lewis pair-functionalized perylenes: the centrosymmetric <b>PBNPf1</b> and the mirror-symmetric <b>PBNPf2</b>. Mirror-symmetric functionalization more effectively tunes the photoelectronic properties. The LUMO energy levels of <b>PBNPf1</b> and <b>PBNPf2</b> are stabilized to -3.00 eV and -3.30 eV. Additionally, the emission maxima of <b>PBNPf1</b> and <b>PBNPf2</b> are shifted to 574 and 628 nm, with fluorescence quantum yields of up to 96% and 87%, respectively.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03015","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report two peri-regioisomers of B←N Lewis pair-functionalized perylenes: the centrosymmetric PBNPf1 and the mirror-symmetric PBNPf2. Mirror-symmetric functionalization more effectively tunes the photoelectronic properties. The LUMO energy levels of PBNPf1 and PBNPf2 are stabilized to -3.00 eV and -3.30 eV. Additionally, the emission maxima of PBNPf1 and PBNPf2 are shifted to 574 and 628 nm, with fluorescence quantum yields of up to 96% and 87%, respectively.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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