Synthesis of an oligo(phenylenevinylene)-bridged phthalocyanine dimer

The nickel phthalocyanine 4, which is soluble in common organic solvents, h as been synthesized from the corresponding tetracyclone monoadduct 1 and ac rolein (3). Reaction of 4 with p-toluenesulfonic acid leads to the modified phthalocyanine monoaldehyde 5. The capability of 5 to undergo a Wittig rea ction has been demonstrated with benzyltriphenylphosphonium bromide (6). Fu rthermore, a dimer 9 has been synthesized by treating 5 with 0.5 equiv. of xylylenebis(triphenylphosphonium bromide) (8). Dimer 9 constitutes a model compound for corresponding PPV polymers containing phthalocyanine subunits.