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Electrochemical diselenation of BODIPY fluorophores for bioimaging applications and sensitization of 1O2

Bozzi, Ícaro A. O., Machado, Luana A., Diogo, Emilay B. T., Delolo, Fábio G., Barros, Luiza O. F., Graça, Gabriela A. P., Araujo, Maria H., Martins, Felipe T., Pedrosa, Leandro F., da Luz, Lilian C., and others. (2023) Electrochemical diselenation of BODIPY fluorophores for bioimaging applications and sensitization of 1O2. Chemistry - A European Journal, 30 (11). Article Number e202303883. ISSN 0947-6539. (doi:10.1002/chem.202303883) (Access to this publication is currently restricted. You may be able to access a copy if URLs are provided) (KAR id:104294)

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We report a rapid, efficient, and scope-extensive approach for the late-stage electrochemical diselenation of BODIPYs. Photophysical analyses reveal red-shifted absorption - corroborated by TD-DFT and DLPNO-STEOM-CCSD computations - and color-tunable emission with large Stokes shifts in the selenium-containing derivatives compared to their precursors. In addition, due to the presence of the heavy Se atoms, competitive ISC generates triplet states which sensitize 1O2 and display phosphorescence in PMMA films at RT and in a frozen glass matrix at 77 K. Importantly, the selenium-containing BODIPYs demonstrate the ability to selectively stain lipid droplets, exhibiting distinct fluorescence in both green and red channels. This work highlights the potential of electrochemistry as an efficient method for synthesizing unique emission-tunable fluorophores with broad-ranging applications in bioimaging and related fields.

Item Type: Article
DOI/Identification number: 10.1002/chem.202303883
Subjects: Q Science
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: National Council for Scientific and Technological Development (
Coordenação de Aperfeicoamento de Pessoal de Nível Superior (
Alexander von Humboldt Foundation (
Deutsche Forschungsgemeinschaft (
Depositing User: Felipe Fantuzzi
Date Deposited: 14 Dec 2023 13:40 UTC
Last Modified: 04 Mar 2024 10:30 UTC
Resource URI: (The current URI for this page, for reference purposes)

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