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

[Image: see text] 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 aldehyd...

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Detalles Bibliográficos
Autores principales: Ventura, Juan, Uriel, Clara, Gómez, Ana M., Avellanal-Zaballa, Edurne, Bañuelos, Jorge, Rebollar, Esther, Garcia-Moreno, Inmaculada, López, J. Cristobal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10127263/
https://www.ncbi.nlm.nih.gov/pubmed/37026858
http://dx.doi.org/10.1021/acs.orglett.3c00476
Descripción
Sumario:[Image: see text] 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 BF(2)-BODIPYs can experience selective aromatic electrophilic substitution (S(E)Ar) 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.