Synthesis and characterization of novel symmetrical phthalocyanines substituted with mono- or bi-macrocycles

A new generation of soluble metallophthalocyanine derivatives (5a, 5b, 6a, 6b, 7b, 8b and 8b·2KSCN) bearing four 14-membered [1,4,8,11] dioxadiaza macrocycles, 14-membered [1,4,8,11] diazadithia-macrocycles or 14-membered [1,4,8,11] diazadithia-macrocycles fused to a 15-membered crown-ether have been prepared by cyclotetramerization of the newly synthesized dicyano macrocycle (3a, 3b and 4b) in the presence of appropriate metal salts in non-aqueous solvents. The N-tosylated derivatives are extensively soluble in apolar solvents. The interaction of the alkaline metal salts with the crown-ether groups of the complex 8b resulted in products of less solubility. Elemental analysis results and IR, UV-Vis, ¹H NMR, mass spectral data on the newly synthesized intermediates and all phthalocyanines are in accordance with the proposed structures. (C) 2000 Elsevier Science Ltd.