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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...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2023
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| 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 |
| _version_ | 1785030426908164096 |
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| author | Ventura, Juan Uriel, Clara Gómez, Ana M. Avellanal-Zaballa, Edurne Bañuelos, Jorge Rebollar, Esther Garcia-Moreno, Inmaculada López, J. Cristobal |
| author_facet | Ventura, Juan Uriel, Clara Gómez, Ana M. Avellanal-Zaballa, Edurne Bañuelos, Jorge Rebollar, Esther Garcia-Moreno, Inmaculada López, J. Cristobal |
| author_sort | Ventura, Juan |
| collection | PubMed |
| description | [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. |
| format | Online Article Text |
| id | pubmed-10127263 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-101272632023-04-26 4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications Ventura, Juan Uriel, Clara Gómez, Ana M. Avellanal-Zaballa, Edurne Bañuelos, Jorge Rebollar, Esther Garcia-Moreno, Inmaculada López, J. Cristobal Org Lett [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. American Chemical Society 2023-04-07 /pmc/articles/PMC10127263/ /pubmed/37026858 http://dx.doi.org/10.1021/acs.orglett.3c00476 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Ventura, Juan Uriel, Clara Gómez, Ana M. Avellanal-Zaballa, Edurne Bañuelos, Jorge Rebollar, Esther Garcia-Moreno, Inmaculada López, J. Cristobal 4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications |
| title | 4,4′-Dicyano-
versus 4,4′-Difluoro-BODIPYs
in Chemoselective Postfunctionalization Reactions: Synthetic Advantages
and Applications |
| title_full | 4,4′-Dicyano-
versus 4,4′-Difluoro-BODIPYs
in Chemoselective Postfunctionalization Reactions: Synthetic Advantages
and Applications |
| title_fullStr | 4,4′-Dicyano-
versus 4,4′-Difluoro-BODIPYs
in Chemoselective Postfunctionalization Reactions: Synthetic Advantages
and Applications |
| title_full_unstemmed | 4,4′-Dicyano-
versus 4,4′-Difluoro-BODIPYs
in Chemoselective Postfunctionalization Reactions: Synthetic Advantages
and Applications |
| title_short | 4,4′-Dicyano-
versus 4,4′-Difluoro-BODIPYs
in Chemoselective Postfunctionalization Reactions: Synthetic Advantages
and Applications |
| title_sort | 4,4′-dicyano-
versus 4,4′-difluoro-bodipys
in chemoselective postfunctionalization reactions: synthetic advantages
and applications |
| url | 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 |
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