Catellani-Inspired BN-Aromatic Expansion: A Versatile Tool toward π-Extended 1,2-Azaborines with Tunable Photosensitizing Properties
BN-isosterism, the replacement of carbon-carbon units with boron-nitrogen pairs in organic frameworks, offers a powerful means to create novel compounds, yet methods to access larger BN-containing polyaromatic cores remain scarce. Leveraging our recently developed multigram-scale synthesis of BN-nap...
| Autores: | , , , , , , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2026 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositório: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/417709 |
| Acesso em linha: | http://hdl.handle.net/10261/417709 https://api.elsevier.com/content/abstract/scopus_id/105028986261 |
| Access Level: | Acceso aberto |
| Palavra-chave: | BN-isosterism Aromatic compounds Fluorescence Hydrocarbons http://metadata.un.org/sdg/11 http://metadata.un.org/sdg/3 http://metadata.un.org/sdg/6 http://metadata.un.org/sdg/9 Ensure healthy lives and promote well-being for all at all ages Ensure availability and sustainable management of water and sanitation for all Build resilient infrastructure, promote inclusive and sustainable industrialization and foster innovation Make cities and human settlements inclusive, safe, resilient and sustainable |
| Resumo: | BN-isosterism, the replacement of carbon-carbon units with boron-nitrogen pairs in organic frameworks, offers a powerful means to create novel compounds, yet methods to access larger BN-containing polyaromatic cores remain scarce. Leveraging our recently developed multigram-scale synthesis of BN-naphthalene, we now combine it with a Catellani-type arene extension (Pd(OAc)2/P(2-furyl)3, norbornene) to rapidly access diverse extended BN-embedded polyaromatic cores. This strategy delivers BN-embedded benzo[c]phenanthridines and curved 8- and 7-membered ring-fused derivatives, as well as BN-embedded benzofluorenones in both normal and inverse BN-vector orientations. Importantly, the ability to access both directional BN isomers, in addition to the parent C═C core, provides a rare opportunity to directly interrogate the effect of the presence and sense of the BN moiety. Most notably, light-induced singlet oxygen (1O2) generation promoted by the benzofluorenone core shows a more than 10-fold enhancement in the "boron-up" BN isostere, while dropping to negligible levels upon inversion of the BN unit. This work thus offers a blueprint for experimental electronic tuning of optically responsive organic materials through BN-mapping. |
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