2-(4-Hydroxy-3,5-dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazole methanol solvate

Abstract

The title compound, C24H22N2O4, was synthesized by the reaction of 9,10‐phenanthraquinone, 4‐hydr­oxy‐3,5‐dimethoxy­benzaldehyde and ammonium acetate in acetic acid. The mol­ecules are linked into a two‐dimensional network by a combination of one N—H⋯O, one O—H⋯N and two O—H⋯O hydrogen bonds.

The synthesis, two-photon absorption and blue upconversion fluorescence of novel, nitrogen-containing heterocyclic chromophores

“…Therefore, it could be suggested that the benzene ring is highly conjugated with the phenanthro[9,10-d]imidazole ring system. Similar geometry has been observed in 2-(4-hydroxy-3,5-dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazole [32], which were reported by us previously. In 2-(4-hydroxy-3,5-dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazole, though the phenanthrene ring is slightly bent, and a dihedral angle of 4.7 is found between the mean planes of the imidazole ring (N1/N2/C9-C11) and phenanthrene ring system (C10-C23), which is larger than that of 3.3 in DS6, these two ring systems are approximately coplanar [r.m.s.…”

10-Hydroxy-10-(1,3-thiazol-2-ylmethyl)phenanthren-9(10H)-one

“…For ring conformations, see: Cremer & Pople (1975). For related structures, see: Jones et al (2002); Li et al (2003); Sun et al (2007); Wang et al (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).…”

“…In recent years, more complex products have been obtained in photoreactions of oxazoles with phenanthrenequinone (Zhang et al, 2004). The crystal structures of 2-(4-hydroxy-3,5-dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazole methanol solvate (Sun et al, 2007) and 2,2,2-tris(cyclohexyloxy)-4,5-(2′,2′′-biphenylo)-1,3,2-dioxaphospholene (Jones et al, 2002) have been reported. Due to the importance of phenanthraquinone derivatives, we report here the crystal structure of the title compound.…”