Artículo
Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
Autor/es | Campos González, René
Vázquez Domínguez, Pablo Remón, Patricia Nájera, Francisco Collado, Daniel Pérez Inestrosa, Ezequiel Boscá, Francisco Ros Lao, Abel Pischel, Uwe |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2022 |
Fecha de depósito | 2022-11-03 |
Publicado en |
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Resumen | 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 ... 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. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España European Research and Development Fund (ERDF) Consejo Superior de Investigaciones Científicas (CSIC) Junta de Andalucía |
Identificador del proyecto | PID2020-119992GB-I00
PID2019-106358GB-C21 PID2019-106358GB-C22 PID2019-110441RB-C33 PID2019-104293GB-I00 202080I005 UMA18-FEDERJA-007 UHU-202070 |
Cita | Campos González, R., Vázquez Domínguez, P., Remón, P., Nájera, F., Collado, D., Pérez Inestrosa, E.,...,Pischel, U. (2022). Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers. Organic Chemistry Frontiers, 9 (16), 4250-4259. https://doi.org/https://dx.doi.org/10.1039/d2qo00778a. |
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