The effect of the fused-ring substituent on anthracene chalcones: crystal structural and DFT studies of 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one and 1-(anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one.

ABSTRACT: The title chalcone compounds, C27H18O (I) and C33H20O (II), were synthesized using a Claisen-Schmidt condensation. Both compounds display an s-trans configuration of the enone moiety. The crystal structures feature inter-molecular C-H?O and C-H?? inter-actions. Quantum chemical analysis of density functional theory (DFT) with a B3LYP/6-311++G(d,p) basis set has been employed to study the structural properties of the compound. The effect of the inter-molecular inter-actions in the solid state are responsible for the differences between the experimental and theoretical optimized geometrical parameters. The small HOMO-LUMO energy gap in (I) (exp?: 3.18?eV and DFT: 3.15?eV) and (II) (exp?: 2.76?eV and DFT: 2.95?eV) indicates the suitability of these compounds for optoelectronic applications. The inter-molecular contacts and weak contributions to the supra-molecular stabilization are analysed using Hirshfeld surface analysis.

SUBMITTER: Zainuri DA 

PROVIDER: S-EPMC5947480 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature