Abstract
The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethyl-ene C=C and carbonyl C=O double bonds in the enone unit. The mol-ecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, mol-ecules are linked into inversion dimers with an R 2 2(10) graph-set motif via pairs of C-H⋯O hydrogen bonds. The inter-molecular inter-actions were analysed and qu-anti-fied by Hirshfeld surface analysis. The mol-ecular structure was optimized and a small HOMO-LUMO energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6-311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV-vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996 (16):0.8004 (16).
Highlights
The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C C and carbonyl C O double bonds in the enone unit
The molecular structure was optimized and a small highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6–311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV–vis analysis
The selection of the organic -system with an electron donor (D) and an electron acceptor (A) is important because it exhibits an essential role in charge transfer in the molecule, where the aromatic groups may lead to delocalization of electronic charge distribution, imparting higher polarization of the push– pull configuration and generation of a molecular dipole (Bures, 2014)
Summary
Conjugated organic molecules with multiple fused aromatic rings have attracted a great deal of interest from researchers because of their excellent performance in organic semiconductor devices (Gu et al, 2015). These organic molecules with a delocalized -system represent attractive targets for applications in light-emitting diodes. An organic chalcone derivative with a conjugated system provides a large transfer axis with appropriate substituent groups on both terminal aromatic rings.
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