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

Year 2018, Volume: 5 Issue: 3, 1375 - 1386, 01.09.2018

Pınar Şen , Salih Zeki Yıldız , Necmi Dege , Göknur Yaşa Atmaca Ali Erdoğmuş , Mustafa Dege

https://doi.org/10.18596/jotcsa.478665

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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