Photo-physicochemical properties of water-soluble non-aggregated indium(III) phthalocyanines.

Abstract

Phthalocyanines have interesting optoelectronic properties but typically suffer from aggregation in aqueous solution, which can limit their applicability, especially in photodynamic therapy. In this study, indium(III) phthalocyanine peripherally substituted with eight triazolyl-containing phenoxy groups (InOAc) and its water-soluble analogue (Q-InOAc) were synthesised and structurally characterised. Heavy metal effects, exerted by the central indium ion, on the photosensitising and photophysical properties (singlet oxygen quantum yield, singlet state lifetime and quantum yield, and triplet state lifetime) were investigated in both DMF and D2O. Highly efficient generation of the triplet excited state (T1), induced by the incorporation of a large atom, enhanced singlet oxygen formation, as revealed by both chemical and physical methods. Correspondingly, the singlet oxygen quantum yield (ΦΔ) of Q-InOAc was 0.603 in DMF and 0.433 in D2O. These values are higher than those previously reported for the corresponding metal-free, Mg-based, and Zn-based water-soluble phthalocyanines (HH, Mg, and Zn). Consequently, Q-InOAc is expected to be an excellent photosensitiser for photodynamic therapy.