Synthesis, electrochemical and photochemical properties of unsymmetrically substituted zinc phthalocyanine complexes

The synthesis of symmetrically and unsymmetrically substituted zinc phthalocyanine (ZnPc) derivatives are reported. The ZnPc derivatives are synthesized by ring expansion of subphthalocyanine complexes. Ring substitution is effected with tert-butyl phenol, naphthol and hydroxybenzoic acid. Comparison of the redox potentials for complexes substituted with varying numbers of tert-butyl phenol: 1 (complex 5), 2 (complex 6), 3 (complex 7), 6 (complex 8) and 8 (complex 9) shows that the complexes with the highest number of substituents are more difficult to oxidize and easier to reduce. All the reported complexes are relatively photostable, with photobleaching quantum yields of the order of 10−5. Singlet oxygen quantum yields for the complexes ranged from 0.22 to 0.68