Synthesis, photochemical and photophysical properties of novel unsymmetrically substituted zinc(II) phthalocyanines

The synthesis of three novel unsymmetrical free base, zinc(II) phthalocyanine derivatives obtained from 3,6-di-(thiophen-3-yl)phthalonitrile and 3,6-didecylphthalonitrile are described. The synthesis of novel 3,6-substituted phthalonitriles bearing heteroaromatic derivatives were achieved through Suzuki-coupling reaction by treatment of 3,6-di(trifluoromethanesulfonyloxy)phthalonitriles and heteroaromatic boronic acids. Two of the newly synthesized complexes showed a high efficiency against a model biological substrate, such as N-acetyl-L-tryptophanamide NATA, and shows a high singlet oxygen quantum yield.