Electrochemical Diselenation of BODIPY Fluorophores for Bioimaging Applications and Sensitization of 1 O 2 .

Autor: Bozzi ÍAO; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Machado LA; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil.; Institute for Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany., Diogo EBT; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Delolo FG; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Barros LOF; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Graça GAP; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Araujo MH; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil., Martins FT; Instituto de Química, Universidade Federal de Goiás, Goiânia, 74690-900, Brazil., Pedrosa LF; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal Fluminense, Volta Redonda, RJ, 27213-145, Brazil., da Luz LC; Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre, 91501-970, RS, Brazil., Moraes ES; Universidade Estadual de Campinas (Unicamp), Cidade Universitária, 13083970 -, Campinas, SP, Brazil., Rodembusch FS; Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre, 91501-970, RS, Brazil., Guimarães JSF; Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil., Oliveira AG; Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil., Röttger SH; DFG Cluster of Excellence livMatS @FIT and Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstraße 21, 79104, Freiburg (Breisgau), Germany., Werz DB; DFG Cluster of Excellence livMatS @FIT and Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstraße 21, 79104, Freiburg (Breisgau), Germany., Souza CP; School of Chemistry and Forensic Science, University of Kent, Park Wood Rd, Canterbury, CT2 7NH, United Kingdom., Fantuzzi F; School of Chemistry and Forensic Science, University of Kent, Park Wood Rd, Canterbury, CT2 7NH, United Kingdom., Han J; Institute for Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany., Marder TB; Institute for Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany., Braunschweig H; Institute for Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany., da Silva Júnior EN; Instituto de Ciências Exatas, Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Feb 21; Vol. 30 (11), pp. e202303883. Date of Electronic Publication: 2024 Jan 18.
DOI: 10.1002/chem.202303883
Abstrakt: 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 1 O 2 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.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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