Decorated BODIPY Fluorophores and Thiol-Reactive Fluorescence Probes by an Aldol Addition.

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.