Synthesis and properties of octa-distyryl-BODIPY substituted zinc(II) phthalocyanines

Abstract

A novel type octa-distyryl-BODIPY substituted zinc(II) phthalocyanines 9 and 10 were prepared by the copper-free Sonogashira coupling and “Click” reactions, respectively. The terminal ethynyl functionalized BODIPY (4,4’-difluoro-8-(4-propynyloxy)-phenyl-1,7-dimethyl-3,5-bis(4-4″-diethylaminophenyl)ethenyl)-4-bora-3a,4a-diaza-s-indacene, 8) compound was reacted with octakis (iodo) zinc(II) phthalocyanine (2) for the synthesis of BODIPY substituted zinc(II) phthalocyanine 9. On the other hand, the same BODIPY compound (8) was used to the synthesis of BODIPY substituted zinc(II) phthalocyanine 10 by the reaction of this BODIPY with octakis-(2-azidoethoxy) zinc(II) phthalocyanine (7). While eight distyryl-BODIPY groups were linked to the phthalocyanine core through ethynyl bonds for phthalocyanine 9, these BODIPY groups were connected to the phthalocyanine core via triazole ring for phthalocyanine 10. All newly synthesized compounds were characterized by elemental analysis and general spectroscopic methods such as 1H NMR, mass, FT-IR, UV–Vis and fluorescence. Moreover, the photophysical and photochemical properties of these conjugates were investigated for determination of their photosensitizer and fluorescence abilities for photodynamic therapy.