Shortcut to Highly Fluorescent Perylene Derivatives: FromFluoranthene Fissure-Coupling to Late-Stage Aromatic Extension
<p>Access to extended perylene-based nanographenes (NGs) is severely limited and involves tedious multi-step synthetic procedures. Here a two-step synthesis shortcut to highly soluble, bent, and extended perylene-based NGs from a nonperylene aromatic homologation precursor is reported. Moreove...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/228176 |
| Acceso en línea: | https://hdl.handle.net/2445/228176 |
| Access Level: | acceso abierto |
| Palabra clave: | Química heterocíclica Química combinatòria Heterocyclic chemistry Combinatorial chemistry |
| Sumario: | <p>Access to extended perylene-based nanographenes (NGs) is severely limited and involves tedious multi-step synthetic procedures. Here a two-step synthesis shortcut to highly soluble, bent, and extended perylene-based NGs from a nonperylene aromatic homologation precursor is reported. Moreover, the resulting scaffold, tetraphenyldibenzoperiflanthene (DBP), is further extended by Pd-based postsynthetic ring fusion, taking advantage of the installation of an aminoquinoline directing group. The rational extension of the DBP scaffold allows synthesizing of highly NIR</p><p>fluorescent pure-red emitters (λem > 700 nm) with excellent quantum yields (ΦFI) up to 0.78. Thorough theoretical analysis sheds light on the correlation between λem, ΦFI, and scaffold molecular editing and extension, showcasing a rational design evolution process toward NGs with desired photophysical properties.</p> |
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