{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Ventura J"],"funding":["Eusko Jaurlaritza","Ministerio de Ciencia e Innovación","European Regional Development Fund"],"pagination":["2588-2593"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10127263"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["25(15)"],"pubmed_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)<sub>2</sub>-BODIPYs displayed enhanced reactivity in Knoevenagel condensations with aldehydes, the corresponding BF<sub>2</sub>-BODIPYs can experience selective aromatic electrophilic substitution (S<sub>E</sub>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."],"journal":["Organic letters"],"pubmed_title":["4,4'-Dicyano- versus 4,4'-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications."],"pmcid":["PMC10127263"],"funding_grant_id":["IT1639-22","PID2020-114755GB-C33","PID2020-114755GB-C31","PID2021-122504NB-I00"],"pubmed_authors":["Ventura J","Rebollar E","Avellanal-Zaballa E","Lopez JC","Uriel C","Garcia-Moreno I","Gomez AM","Banuelos J"],"additional_accession":[]},"is_claimable":false,"name":"4,4'-Dicyano- versus 4,4'-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications.","description":"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)<sub>2</sub>-BODIPYs displayed enhanced reactivity in Knoevenagel condensations with aldehydes, the corresponding BF<sub>2</sub>-BODIPYs can experience selective aromatic electrophilic substitution (S<sub>E</sub>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.","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Apr","modification":"2025-04-22T18:03:47.046Z","creation":"2025-04-22T18:03:47.046Z"},"accession":"S-EPMC10127263","cross_references":{"pubmed":["37026858"],"doi":["10.1021/acs.orglett.3c00476"]}}