A novel entry to meso-decorated BODIPY motifs on the basis of an unusual aldol-type addition with diethyl ketomalonate is reported. The evolving β-hydroxyl group can be optionally eliminated, which suppresses the fluorescence of the BODIPY core by attachment of a π-electronically coupled methylidene malonate unit. This unit serves as a versatile, highly electrophilic acceptor platform for various nucleophilic additions. Corresponding products benefit from a fully restored fluorescence.
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