Academic Journal
Light-induced Ligation of o-Quinodimethanes with Gated Fluorescence Self-reporting
| العنوان: | Light-induced Ligation of o-Quinodimethanes with Gated Fluorescence Self-reporting |
|---|---|
| المؤلفون: | Feist, Florian, Rodrigues, Leona L., Walden, Sarah L., Krappitz, Tim W., Dargaville, Tim R., Weil, Tanja, Goldmann, Anja S., Blinco, James P., Barner-Kowollik, Christopher |
| المصدر: | Journal of the American Chemical Society, 142 (17), 7744–7748 ; ISSN: 0002-7863, 1520-5126 |
| بيانات النشر: | American Chemical Society |
| سنة النشر: | 2024 |
| المجموعة: | KITopen (Karlsruhe Institute of Technologie) |
| مصطلحات موضوعية: | Absorption, Addition reactions, Aromatic compounds, Fluorescence, Hydrocarbons, ddc:600, Technology, info:eu-repo/classification/ddc/600 |
| الوصف: | We introduce a highly efficient photoligation system, affording a pro-fluorescent Diels–Alder product that, on demand, converts into an intensively fluorescent naphthalene via E1 elimination in the presence of catalytic amounts of acid. The Diels–Alder reaction of the photocaged diene (o-quinodimethane ether or thioether) with electron-deficient alkynes is induced by UV or visible light. In contrast to previously reported ligation techniques directly leading to fluorescent products, the fluorescence is turned on after the photoligation. Thus, the light absorption of the fluorophore does not undermine the photoligation via competitive absorption, and as a result, photobleaching or side reactions of the fluorophore are not observed. Critically, the gated generation of a fluorescent product allows for fluorometric determination of the conversion. We employ a simple synthesis strategy for heterobifunctional electron-deficient alkynes allowing for facile functionalization of payload molecules. |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/wos/000529959000006; info:eu-repo/semantics/altIdentifier/issn/0002-7863; info:eu-repo/semantics/altIdentifier/issn/1520-5126; https://publikationen.bibliothek.kit.edu/1000175292; https://publikationen.bibliothek.kit.edu/1000175292/155391971; https://doi.org/10.5445/IR/1000175292 |
| DOI: | 10.5445/IR/1000175292 |
| الاتاحة: | https://publikationen.bibliothek.kit.edu/1000175292 https://publikationen.bibliothek.kit.edu/1000175292/155391971 https://doi.org/10.5445/IR/1000175292 |
| Rights: | KITopen License, https://publikationen.bibliothek.kit.edu/kitopen-lizenz ; info:eu-repo/semantics/openAccess |
| رقم الانضمام: | edsbas.F49B89AD |
| قاعدة البيانات: | BASE |
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