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

Journal of the Turkish Chemical Society, Section A: Chemistry

Ali Erdoğmuş¹  Göknur Yaşa Atmaca¹  Necmi Dege²  Pınar Şen³  Salih Zeki Yıldız³  Mustafa Dege⁴ 

[1] Department of Chemistry, Yildiz Technical University, 34210 Esenler, Istanbul, Turkey;Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139 Samsun, Turkey;Sakarya University, Faculty of Arts and Sciences, Department of Chemistry, 54187, Sakarya,Turkey;Spraying Systems Company, Kaya Aldoğan sok. No: 3/3 34394Zincirlikuyu Şişli - İstanbul, Turkey;

关键词: Synthesis;    benzimidazole derivative;    Schiff base;    Single crystal;    X-ray crystallography;    Crystal structure;    Fluorescence property;   

DOI  :  10.18596/jotcsa.478665

来源: DOAJ

【 摘 要 】

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 systemis 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.

【 授权许可】

Unknown