Synthesis and characterization of novel metal-free and metallophthalocyanines diazadioxamacrocycles

New metal-free phthalocyanines fused in peripheral positions with eight N-monotosylated diaza-12-crown-4 macrocyclic moieties connected by diethylenethio groups have been synthesized by cyclotetramerization of a newly synthesized dicyano-substituted macrocycle. Metallophthalocyanines were also prepared by reaction of the dicyano-substituted macrocycle in the presence of corresponding metal salts and a strong organic base. The new compounds were characterized by a combination of elemental analysis, H-1 and C-13 NMR, IR, electronic and mass spectroscopies.