The synthesis and characterization of new metal-free and metallophthalocyanines containing four 27-membered diazaheptathia macrocycles

A new metal-free 5 and metallophthalocyanines 6 and 7 containing four 27-membered diazaheptathia macrocyclic moieties on peripheral positions have been synthesized. The metal-free phthalocyanine 5 was synthesized by the reaction 27,28-dicyano-9,10,12,13,23,24,31,32-octahydro-5H,15H-tribenzo[b,h,w][1,4,7,13,16,19,25,10,22]heptathia diazacycloheptacosine-6,16 (7H,17H)-dione 4 with anhydrous 2-(dimethylamino)ethanol under reflux for 28 h. Metallophthalocyanines 6 and 7 were synthesized by the reaction of 4 with anhydrous NiCl2 and Zn(CH3CO)2 in dry quinoline, respectively. The new compounds were characterized by a combination of elemental analysis and 1H NMR, 13C NMR, IR, UV–vis and MS spectral data.