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

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)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.

SUBMITTER: Ventura J 

PROVIDER: S-EPMC10127263 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature