Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers. Issue 16 (29th June 2022)

• Record Type: Journal Article
• Authors: Campos-González, René; Vázquez-Domínguez, Pablo; Remón, Patricia; Nájera, Francisco; Collado, Daniel; Pérez-Inestrosa, Ezequiel; Boscá, Francisco; Ros, Abel; Pischel, Uwe
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 16(2022)
• Page Start: 4250
• Page End: 4259
• Publication Date: 2022-06-29
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00778a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Polycyclic aromatic hydrocarbon chromophores that show an ideal bipartition between fluorescence and singlet oxygen production have been developed. Abstract : Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores are obtained by a bromination–borylation sequence. The bis-borylated dyes show red-shifted absorption ( λ abs, max > 450 nm) and emission ( λ f, max > 500 nm; Φ f : 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 ( Φ Δ : 0.50–0.66). This bipartition provides the setting for the concomitant observation of fluorescence and photosensitization, making these dyes ideal bimodal chromophores.