Synthesis of diiodo butadiynyl-bridged bisphthalocyaninatozinc(II) complexes

Two functionalized phthalocyanine-based chromophore systems having two iodophthalocyaninatozinc(II) rings bound together through a butadiynyl linkage 1a,b have been synthesized by oxidative Eglinton coupling of the corresponding monomer, and fully characterized. The electronic characteristics of these extensively linearly π-conjugated compounds were modulated by the introduction of different peripheral substituents into the phthalocyanine moieties and investigated by UV–visible spectroscopy. The reactivity of the two iodo substituents was explored to prepare a novel bisphthalocyanine containing two ethynylphenyl moieties, thus pointing out the possibility of incorporating other electro and/or photoactive moieties in the BisPc system, taking advantage of the iodo-functionalization.