Mono-functionalized dibenzo[g,p]-chrysenes for cascade energy transfer

3-Bromodibenzo[g,p]chrysene has been synthesized in a one-pot reaction using phenyliodine(III) bis(trifluoroacetate) (PIFA) as an oxidant and a Lewis acid. The bromo function was easily converted to the cyano, alkyne, and formyl derivatives. Bodipy dyes have either been constructed from the chrysene-aldehyde or by cross coupling reactions with the chrysene ethynyl derivatives. The linking of diketopyrrolopyrrole (DPP) fragments was realized using the chrysene-ethynyl compound or with the in situ prepared chrysene-borolane derivatives. The novel chrysene dyes are highly fluorescent in apolar solvents and were used as input energy in intramolecular energy transfer processes with covalently linked DPP or Bodipy dyes. All mixed dyes are redox active and each module is clearly identified by its redox behavior. Little electronic interaction is evidenced whatever the nature of the dyes and spacer. (c) 2013 Elsevier Ltd. All rights reserved.