Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption (λabs,max > 450 nm) and emission (λf,max > 500 nm; Φf: 0.3–0.5) properties as compared to the parent PAHs. Their centro...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2022 |
| País: | España |
| Institución: | Universidad de Sevilla (US) |
| Repositorio: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:idus.us.es:11441/138677 |
| Acceso en línea: | https://hdl.handle.net/11441/138677 https://doi.org/10.1039/d2qo00778a |
| Access Level: | acceso abierto |
| Sumario: | Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption (λabs,max > 450 nm) and emission (λf,max > 500 nm; Φf: 0.3–0.5) properties as compared to the parent PAHs. Their centrosymmetric A–π-A (A: acceptor) structures led to the observation of two-photon absorption (up to 60 GM) in the near-infrared spectral region (>800 nm). The rigid structure shuts down non-radiative deactivation by limiting rotational or vibrational freedom. Thus, the excited-state pathways originating from the excited singlet state are resumed to fluorescence and excited triplet-state formation. The latter is involved in the energy-transfer sensitization of singlet oxygen (ΦΔ: 0.50–0.66). This bipartition provides the setting for the concomitant observation of fluorescence and photosensitization, making these dyes ideal bimodal chromophores. |
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