Novel symmetrically tetrasubstituted metal-free and metallophthalocyanines (5) and (6) which contain four hexaazadioxamacrobicycles on peripheral positions, have been synthesized. Macrobicyclic compound 3 and has been prepared by reaction of (1,3,6,9,11,14- hexaazatricyclo[12.2. 1.1(6,9)])octadecane (1) with 1,2-bis(2-iodoethoxy)-4,5-dibromobenzene (2). Compound 4 has been synthesized by reaction of compound 3 with CuCN in dry DMF. The target symmetrical phthalocyanines were separated by column chromatography and characterized by elemental analyses, H-1, C-13-NMR, IR, UV-Visible and FAB mass spectroscopies.