The synthesis of novel directly conjugated zinc(II) phthalocyanine via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction and its quaternized water-soluble derivative: Investigation of photophysical and photochemical properties

Abstract

The novel zinc(II) phthalocyanine directly conjugated with 4-(diethylamino)phenyl groups (2) via C-C bond formation using Suzuki-Miyaura coupling reaction was synthesized for the first time. This phthalocyanine was converted to the quaternized derivative (3) to enhance its water solubility. The photochemical (singlet oxygen quantum yield and photodegradation quantum yield) and photophysical (fluorescence quantum yield and lifetime) properties of the synthesized novel zinc(II) phthalocyanines (2 and 3) were investigated in DMSO (for both phthalocyanines 2 and 3) and in aqueous solution (for only phthalocyanine 3) for determination of their photodynamic therapy abilities. Additionally, the bovine serum albumin (BSA) binding behavior of the water soluble zinc(II) phthalocyanine (3) was investigated in aqueous solution for determination of transporting capability of this phthalocyanine in the circulatory system. (C) 2016 Elsevier Ltd. All rights reserved.