Synthesis, characterization and biological activities of new metal-free and metallo phthalocyanines containing triazole group

In this study, phthalocyanine precursors (5 and 9) and 1,2,3-triazole-substituted metal-free and metallophthalocyanines (9a-c) were synthesized for the first time. Firstly, 2-(2-azido-ethoxy)-ethanol (1) was synthesized according to the literature. Then, the copper catalyzed reaction of this compound with 4-ethynylpyridine hydrochloride gave compound 5 containing the 1,2,3-triazole ring. In the third step of the synthesis, the phthalonitrile compound 9 was synthesized from SNAr like reaction of compound 5 with 4-nitrophthalonitrile. Finally, metal-free (9a) and metallo (9b and 9c) phthalocyanines were synthesized by direct cyclotetramerization of phthalonitrile. The structures of all compounds were characterized via FT-IR, 1H/13C NMR, UV-Vis, and MS. In the application step, the inhibition effects of these compounds on acetylcholinesterase enzyme were investigated.