Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores

Boradiazaindacenes with methyl substituents at 3 and 5 positions were for the first time shown to undergo efficient double condensation reactions with an aromatic aldehyde yielding a series of extended conjugation dyes. These new fluorophores have absorption maxima in the range of 650–660 nm. The dyes reported here have large quantum yields with 20 nm Stokes' shifted emission peaks. The straightforward synthesis of such red shifted BODIPY derivatives is important in relation to the synthesis of novel and useful fluorescent chemosensors. In addition, this facile transformation may make these new fluorophores' building blocks in the construction of large functional supramolecular systems.