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.

 

Keywords

• Synthesis,benzimidazole derivative,Schiff base,Single crystal,X-ray crystallography,Crystal structure,Fluorescence property

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