Synthesis of nickel(II) triazolenaphthalocyanine and related macrocycles

The synthesis of novel monbenzotriazolephthalocyanines (3-6), low-symmetry phthalocyanine analogues, is described for the first time using a novel and simple stepwise strategy which involves the use of substituted naphthalodinitriles 8-11 and appropriately substituted three-unit compounds such as 7. Belonging to the same family, compound 1, which we have called triazolenaphthalocyanine, has been prepared by a statistical method from compound 2 and 3,5-diamino-1,2,4-triazole. Compound 1 shows a bathochromic shift of the Q-band in UV-vis spectrum due to the fusing of benzene rings to the triazolephthalocyanine core.