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

dc.contributor.authorVentura, Juan
dc.contributor.authorUriel, Clara
dc.contributor.authorGómez López, Ana María
dc.contributor.authorAvellanal Zaballa, Edurne
dc.contributor.authorBañuelos Prieto, Jorge ORCID
dc.contributor.authorRebollar, Esther ORCID
dc.contributor.authorGarcía Moreno, Inmaculada
dc.contributor.authorLópez Pérez, José Cristóbal
dc.date.accessioned2023-05-15T12:02:26Z
dc.date.available2023-05-15T12:02:26Z
dc.date.issued2023-04
dc.identifier.citationOrganic Letters 25(15) : 2588-2593 (2023)es_ES
dc.identifier.issn1523-7060
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10810/61113
dc.description.abstractThe 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.es_ES
dc.description.sponsorshipThe 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.es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2021-122504NB-I00es_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C31es_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C33es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.title4,4′-Dicyano- versus 4,4′-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applicationses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0)es_ES
dc.rights.holderAtribución 3.0 España*
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c00476es_ES
dc.identifier.doi10.1021/acs.orglett.3c00476
dc.departamentoesQuímica físicaes_ES
dc.departamentoeuKimika fisikoaes_ES


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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)