Unprecedented chemosensing behavior of novel tetra-substituted benzimidazole zinc(II) phthalocynine for selective detection of Bi3+ ion: Synthesis, characterization and ROS generation

Abstract

In this work, synthesis of novel symmetrical 4-(2-bromo-4-(5-bromo-1H-benzo[d] imidazol-2-yl) phenoxy) tetra substituted zinc phthalocyanine has been reported. The novel benzimidazole zinc phthlocynine compound (3) has been characterized by MALDI-TOF MS, FT-IR, UV-vis, and ¹H NMR spectroscopy. This new compound 3 displayed excellent selectivity towards Bi³⁺ ion in the presence of other competitive ions including Ca²⁺, Cd²⁺, Co²⁺ Cu²⁺, Fe³⁺, Hg²⁺, Sn²⁺, Mg²⁺, Na⁺, Ni²⁺ and Pb²⁺ respectively. Upon addition of Bi³⁺ into the solution of compound 3 in DMSO, dramatic change was observed in the Q- and the B-bands in UV-visible spectra as a result of donor acceptor interactions. Reactive oxygen species (ROS) were also studied using 2,7-dichlorofluorescin diacetate (DCFH-DA) a fluorescent probe which is converted to highly fluorescent dichlorofluorescein (DCF) in the presence of ROS. This property of non-aggregating zinc phthalocyanine is promising as a photosensitizer in photodynamic therapy of cancer.

Keywords: Bi(3+); Chemosensor; Reactive oxygen species; Zinc phthalocyanine.