biostudies-literatureVentura JEusko JaurlaritzaMinisterio de Ciencia e InnovaciónEuropean Regional Development Fund2588-2593https://www.ebi.ac.uk/biostudies/studies/S-EPMC10127263biostudies-literatureUnknown25(15)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 (S_EAr) 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.Organic letters4,4'-Dicyano- versus 4,4'-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications.PMC10127263IT1639-22PID2020-114755GB-C33PID2020-114755GB-C31PID2021-122504NB-I00Ventura JRebollar EAvellanal-Zaballa ELopez JCUriel CGarcia-Moreno IGomez AMBanuelos Jfalse4,4'-Dicyano- versus 4,4'-Difluoro-BODIPYs in Chemoselective Postfunctionalization Reactions: Synthetic Advantages and Applications.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 (S_EAr) 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.2023-01-01T00:00:00Z2023 Apr2025-04-22T18:03:47.046Z2025-04-22T18:03:47.046ZS-EPMC101272633702685810.1021/acs.orglett.3c00476