{"title":"Near-Infrared Twisted Polycyclic Arene-Fused BisBODIPYs through a Tandem Inter- and Intramolecular Scholl Reaction","authors":"Huiquan Zuo, Qinghua Wu, Long Wang, Zhengxin Kang, Heng Li, Hua Wang, Xing Guo, Jiangang Gao, Erhong Hao, Lijuan Jiao","doi":"10.1021/acs.orglett.5c00311","DOIUrl":null,"url":null,"abstract":"Five novel polyaromatic-ring-fused bisBODIPYs have been synthesized from corresponding readily available α-arylBODIPYs through a FeCl<sub>3</sub>-mediated tandem inter- and intramolecular oxidative aromatic coupling reaction. These resultant bisBODIPYs show twisted planar conformations, strong absorptions (ε up to 1.8 × 10<sup>5</sup> M<sup>–1</sup> cm<sup>–1</sup>), and good fluorescence emissions in the near-infrared region (NIR, 660–734 nm) and good intersystem crossing efficiencies (Φ<sub>Δ</sub> = 18.9% for dimer <b>2d</b> in toluene), demonstrating their promising potential applications as heavy-atom-free photosensitizers.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-25","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.5c00311","RegionNum":1,"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
Five novel polyaromatic-ring-fused bisBODIPYs have been synthesized from corresponding readily available α-arylBODIPYs through a FeCl3-mediated tandem inter- and intramolecular oxidative aromatic coupling reaction. These resultant bisBODIPYs show twisted planar conformations, strong absorptions (ε up to 1.8 × 105 M–1 cm–1), and good fluorescence emissions in the near-infrared region (NIR, 660–734 nm) and good intersystem crossing efficiencies (ΦΔ = 18.9% for dimer 2d in toluene), demonstrating their promising potential applications as heavy-atom-free photosensitizers.
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.
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