A new multifunctional benzimidazole tagged coumarin as ratiometric fluorophore for the detection of Cd2+/F- ions and imaging in live cells

Abstract

A novel multifunctional ratiometric fluorescent probe has been designed and synthesized for the selective recognition of Cd²⁺/F^- ions. The probe (3)-((2)-(1H-benzoimidazole-2-yl)-phenylimino) methyl-4-chloro-methyl-2H-chromen-2-ene (BIMC) displays excellent ratiometric responses towards Cd²⁺/F^- ions over the tested cations/anions. The lowest detection limits observed for Cd²⁺ and F^- are 1.5 × 10^-10 mol/l and 1.2 × 10^-10 mol/l respectively. Job's plot and Electro spray Ionization mass spectral (ESI-MS) studies confirms 1:1 binding stoichiometry of BIMC with Cd²⁺/F^- ions, which is further evidenced by ¹H NMR titration studies. The reversibility studies of BIMC with Cd²⁺ have been investigated using ethylenediaminetetraacetic acid (EDTA). Upon binding to Cd²⁺/F^- ions, the probe features strong ratiometric response in both UV-Visible and fluorescence spectra due to the inhibition of intramolecular charge transfer (ICT). Furthermore, the mechanism of ICT has been rationalized via solvatochromism and DFT calculations.

Keywords: DFT calculations; Dual sensor; Live cell imaging; Ratiometry; Solvatochromism.