Synthesis and characterization of a new zinc phthalocyanine containing macrobicyclic moieties

Novel zinc phthalocyanine (ZnPc) containing symmetrically eight triaza-tetraoxa macrobicycles on peripheral positions has been synthesized in a multistep reaction sequence. The cyclotetramerization reaction was accomplished with 4,5-bis[2-(4,7,13,16-tetraoxa-1,10,22-triazabicyclo[8.8.7]pentacosane-22- yl)ethylthio]phthalonitrile (6) which was prepared by the reaction of 1,2-bis(2-iodoethoxy)-4,5-dicyanobenzene (5) and 4,7,13,16-tetraoxa-1,10,22- triazabicyclo[8.8.7]pentacosane (4). The novel compounds were characterized by a combination of elemental analysis, 1H and 13C NMR, IR, UV-vis and MS spectral data. © 2013 Elsevier B.V