Abstract
The title compounds, 2-(4-hexyl-oxyphen-yl)-1H-benzimidazole (C19H22N2O; 1), 2-(4-hexyl-oxyphen-yl)-1-phenyl-1H-benzimidazole (C25H26N2O; 2) and 1-benzyl-2-(4-hexyl-oxyphen-yl)-1H-benzimidazole (C26H28N2O; 3) were synthesized and their structures were determined by single-crystal X-ray analysis. The N-substituent at the imidazole moiety slightly affects the inter-planar angle between the 4-hexyl-oxyphenyl ring and the benzimidazole system. The unsubstituted benzimidazole (1) forms inter-molecular N-H⋯N bonds while in the crystal structures of 2 and 3, the mol-ecules are assembled only through π-π and C-H⋯π inter-actions.
Highlights
2-Arylbenzimidazoles have attracted considerable attention as biologically active compounds (Vasava et al, 2020)
The benzimidazole systems are essentially flat while the alkoxyaryl rings are inclined to them with dihedral angles of 35.02 (17), 31.46 (4) and 38.67 (6) for 1, 2 and 3, respectively
The N-phenyl ring is expected to exert a larger steric pressure in 2 as compared with 3, its rotation by 68.92 (4) along the N2—C8 bond seems to reduce the steric hindrance in the molecule and results in the smallest interplanar angle between the aryl and imidazole moieties in the series
Summary
2-Arylbenzimidazoles have attracted considerable attention as biologically active compounds (Vasava et al, 2020) They are used as ligands in constructing cyclometalated iridium(III) and ruthenium(II) complexes for organic lightemitting diodes and photosensitizers in dye-sensitized solar cells (Bezzubov et al, 2020; Lavrova et al, 2020). For the latter application, the aryl unit of these ligands should contain -electron-donating substituents to increase the lightharvesting characteristics of the corresponding organometallic complexes (Aghazada & Nazeeruddin, 2018; Bezzubov et al, 2014, 2016). We synthesized 2-(4-hexyloxyphenyl)-1H-benzimidazole (1) and its N-phenyl and N-benzyl analogues (2 and 3, respectively) and studied their crystal structures
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