RT Journal Article
T1 Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
A1 Campos González, René
A1 Vázquez Domínguez, Pablo
A1 Remón Ruiz, Patricia
A1 Nájera, Francisco
A1 Collado, Daniel
A1 Pérez Inestrosa, Ezequiel
A1 Boscá Mayans, Francisco
A1 Ros, Abel
A1 Pischel, Uwe
AB 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.
PB Royal Society of Chemistry
SN 2052-4129
YR 2022
FD 2022
LK https://hdl.handle.net/10272/21612
UL https://hdl.handle.net/10272/21612
LA eng
NO Campos-González, R., Vázquez-Domínguez, P., Remón, P., Nájera, F., Collado, D., Pérez-Inestrosa, E., Boscá, F., Ros, A., & Pischel, U. (2022). Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers. In Organic Chemistry Frontiers (Vol. 9, Issue 16, pp. 4250–4259). Royal Society of Chemistry (RSC). https://doi.org/10.1039/d2qo00778a
NO We are grateful for financial support from the Spanish Ministerio de Ciencia e Innovación (grant PID2020-119992GB-I00 for U. P., PID2019-106358GB-C21 and PID2019-106358GB-C22 for A. R., PID2019-110441RB-C33 for F. B., PID2019-104293GB-I00 for F. N and E. P.-I, and doctoral fellowship PRE2020-092646 for P. V.-D.), the European Research and Development Fund (ERDF), the Consejo Superior de Investigaciones Científicas (grant 202080I005 for A. R.), the Junta de Andalucía/University of Malaga (grant UMA18-FEDERJA-007 for F. N. and E. P.-I.), and the Junta de Andalucía/University of Huelva (grant UHU-202070 for U. P.). Dr Z. Domínguez (University of Huelva) is acknowledged for technical assistance in the early phase of this work.
DS Repositorio Institucional de la Universidad de Huelva
RD 1 jun 2026