Issue 16, 2022

Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

Abstract

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.

Graphical abstract: Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

Supplementary files

Article information

Article type
Research Article
Submitted
13 may 2022
Accepted
19 iyn 2022
First published
29 iyn 2022
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2022,9, 4250-4259

Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

R. Campos-González, P. Vázquez-Domínguez, P. Remón, F. Nájera, D. Collado, E. Pérez-Inestrosa, F. Boscá, A. Ros and U. Pischel, Org. Chem. Front., 2022, 9, 4250 DOI: 10.1039/D2QO00778A

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