4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications

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Date
2023-04
Author
Ventura, Juan
Uriel, Clara
Gómez López, Ana María
Avellanal Zaballa, Edurne
Bañuelos Prieto, Jorge ORCID
Rebollar, Esther ORCID
García Moreno, Inmaculada
López Pérez, José Cristóbal
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  Estadisticas en RECOLECTA
(LA Referencia)

Organic Letters 25(15) : 2588-2593 (2023)
URI
http://hdl.handle.net/10810/61113
Abstract
The presence of F or CN substituents at boron in BODIPYs causes a dramatic effect on their reactivity, which allows their chemoselective postfunctionalization. Thus, whereas 1,3,5,7-tetramethyl B(CN)2-BODIPYs displayed enhanced reactivity in Knoevenagel condensations with aldehydes, the corresponding BF2-BODIPYs can experience selective aromatic electrophilic substitution (SEAr) reactions in the presence of the former. These (selective) reactions have been employed in the preparation of BODIPY dimers and tetramers, with balanced fluorescence and singlet oxygen formation, and all-BODIPY trimers and heptamers, with potential application as light-harvesting systems.
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© 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)
Except where otherwise noted, this item's license is described as © 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)