Compounds with polarizable pi systems that are susceptible to attack with nucleophiles at C-Hal (Hal = Cl, Br) bonds react with Pd(PPh3)(4) to yield net oxidative addition. X-ray structures show that the resulting Pd.(PPh3)(2)Hal groups greatly reduce intermolecular interactions. The Pd-functionalited dyes generally exhibit solution-like absorption spectra in films, whereas their Hal analogues exhibit features attributable to aggregation.