Synthesis and characterization of new organosoluble metal-free and metallophthalocyanines substituted by four macrocycles containing piperazine moiety

The syntheses of metal-free phthalocyanine 3 and metallophthalocyanines 4 and 5 with four 12-membered dithiadiaza macrocycles containing piperazine moiety on peripheral position have been accomplished by cyclotetramerization of 1,4-bis(2-(4,5-dicyano-1,2-pheylene)sulfanediyl)piperazine-2,5-dione 2. The formation of macrocycle containing piperazine subunit 2 did not require a high dilution technique or template effect and was performed by the reaction of 1 containing N-substituted 2-chloroamide moiety and sodium hydroxide in DMF. Metal-free phthalocyanine and metallophthalocyanines showed the enhanced solubility in organic solvents. These new compounds were characterized by a combination of elemental analysis and 1H NMR, 13C NMR, IR, UV–vis and MS spectral data.