Crystal structures, DFT studies and UV-visible absorption spectra of two anthracenyl chalcone derivatives

Abstract

The crystal structures of (E)-1-(anthracen-9-yl)-3-(3H-indol-2-yl)prop-2-en-1-one, C 25 H 17 NO, and (E)-1-(anthracen-9-yl)-3-[4-(dimethylamino)naphthalen-1-yl]prop-2-en-1-one, C 29 H 23 NO, are reported. In each case the anthracene ring system and pendant ring system are almost perpendicular to each other [dihedral angles = 75.57 (7)° and 70.26 (10)°, respectively]. In the extended structures, weak N - H⋯O, C - H⋯O and C - H⋯π interactions influence the centrosymmetric crystal packing. Density functional theory calculations were carried out using a 6-311 G++(d,p) basis set and the calculated structures are in good agreement with the crystal structures. The compounds were also characterized by UV-Vis absorption spectroscopy and the smallest (HOMO-LUMO) energy gaps of 2.89 and 2.54 eV indicate the enhanced non-linear responses (intermolecular charge transfers) of these systems.