4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications
| Autor: | Juan Ventura, Clara Uriel, Ana M. Gómez, Edurne Avellanal-Zaballa, Jorge Bañuelos, Esther Rebollar, Inmaculada Garcia-Moreno, J. Cristobal López |
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| Rok vydání: | 2023 |
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| Zdroj: | Organic Letters. 25:2588-2593 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.3c00476 |
| Popis: | 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. The authors gratefully acknowledge Spanish Ministerio de Ciencia e Innovación (MCIN)/Agencia Estatal de Investigación (AEI) Grant PID2021-122504NB-I00 funded by MCIN/AEI/10.13039/501100011033 and by ERDF A way of making Europe and Grants PID2020-114755GB-C31 and -C33 funded by MCIN/AEI. The authors thank the Gobierno Vasco (Project IT1639-22) for financial support. The authors are indebted to Ms. Marina Rodríguez (IQOG-CSIC) for skillful technical support. |
| Databáze: | OpenAIRE |
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