Synthesis and crystal structures of N-H, N-phenyl and N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles

Abstract

The title compounds, 2-(4-hexyloxyphenyl)-1H-benzimidazole (C19H22N2O; 1), 2-(4-hexyloxyphenyl)-1-phenyl-1H-benzimidazole (C25H26N2O; 2) and 1-benzyl-2-(4-hexyloxyphenyl)-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 interplanar angle between the 4-hexyloxyphenyl ring and the benzimidazole system. The unsubstituted benzimidazole (1) forms intermolecular N—H...N bonds while in the crystal structures of 2 and 3, the molecules are assembled only through π–π and C—H...π interactions.

Tailoring the π-system of benzimidazole ligands towards stable light-harvesting cyclometalated iridium(iii) complexes

“…76 1-Benzyl-2-phenyl-[2,3]-naphtimidazole ( bni ) was synthesized according to published procedure. 77 1 H and 13 C{ 1 H} NMR spectra of cyclometalated ligands are presented in Fig. S1–S10 †.…”

Rational design of efficient photosensitizers based on cyclometalated iridium(iii) complexes with 2-arylbenzimidazole and aromatic 1,3-diketone ligands

“…The target benzimidazoles were synthesized by previously described condensation of N -phenyl- o -phenylenediamine with aromatic aldehydes in the presence of Na 2 S 2 O 5 . 41 However, for the reaction with aldehydes containing strongly electron-withdrawing fluoro- and trifluoromethyl-substituents, a stronger oxidant was required. The synthesis of the corresponding benzimidazoles was implemented according to a procedure requiring hydrogen peroxide and NBu 4 I.…”