Versatile Metal-Free Arylation of BODIPY and Bis(BF 2 ) Chromophores by Using Arylazosulfones in a Sunflow System.

Autor: de Melo SMG; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil., Dos Santos T; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.; Center of Research and Advancements in Fragments and Molecular Targets-CRAFT, FCFRP-USP, Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil., Silva DG; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.; Center of Research and Advancements in Fragments and Molecular Targets-CRAFT, FCFRP-USP, Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil., Martins YA; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil., Eckhardt P; Department of Chemistry, Johannes Gutenberg University, Mainz, Duesbergweg 10-14, Mainz, 55128, Germany., Lopez RFV; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil., Opatz T; Department of Chemistry, Johannes Gutenberg University, Mainz, Duesbergweg 10-14, Mainz, 55128, Germany., Protti S; PhotoGreen Lab, Department of Chemistry, Viale Taramelli 12, 27100, Pavia, Italy., da Silva Emery F; Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.; Center of Research and Advancements in Fragments and Molecular Targets-CRAFT, FCFRP-USP, Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Nov 04; Vol. 30 (61), pp. e202402634. Date of Electronic Publication: 2024 Oct 04.
DOI: 10.1002/chem.202402634
Abstrakt: BODIPYs have a well-established role in biological sciences as chemosensors and versatile biological markers due to their chemical reactivity, which allows for fine-tuning of their photophysical characteristics. In this work, we combined the unique reactivity of arylazo sulfones with the advantages of a "sunflow" reactor to develop a fast, efficient, and versatile method for the photochemical arylation of BODIPYs and other chromophores. This approach resulted in red-shifted emitting fluorophores due to extended electronic delocalization at the 3- and 5-positions of the BODIPY core. This method represents an advantageous approach for BODIPY functionalization compared to existing strategies.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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