A novel Benzimidazole moiety-appended Schiff base derivative: Synthesis, characterization and the investigation of photophysical and chemosensor properties

Abstract

In this study, we synthesized a novel benzimidazole-based Schiff base; (E)-4,4'-methylenebis(2-((E)-(((1H-benzo[d]imidazol-2-yl)methyl)imino)methyl)phenol) (3) was synthesized by the condensation of 5,5'-methylenebis(2-hydroxybenzaldehyde) (1) and (1H-benzo[d]imidazol-2-yl)methanamine.HCl salt (2). This Schiff base derivative was reported for the first time and was fully characterized by FT-IR, UV–vis, 1H-NMR, 13C-NMR and mass spectroscopy. Electronic absorption and fluorescence titration studies of 3 with different metal cations in a DMF show a highly selective binding affinity only toward and Zn2+ ion. The crystal structure of 2, C8H13Cl2N3O, has been determined by single crystal X-ray diffraction method. The crystal structure of the title compound, C8H11N32+×2(Cl—)×H2O, consists of an organic 1H-benzoimidazol-3-ium (C8H11N32+) cation, an inorganic 2(Cl—) anion and one water (H2O) molecule. In the cation of the title compound, C8H11N32+, the benzimidazole ring system is planar with a maximum deviation of -0.012 (3) Å. The crystal belongs to monoclinic system, space group P21/c. The crystal packing is stabilized by intramolecular N–H···O, N–H···Cl, the intermolecular N–H···Cl interactions link the molecules into a two-dimensional network and between anions and the water molecules. π-π contacts between benzimidazole rings [centroid–centroid distances = 3.4642 (2) Å, 3.5309 (2) Å and 3.5527 (2) Å] may further stabilize the structure.