Abstract
The mol-ecular and crystal structure of two new chalcone derivatives, (E)-1-(anthracen-9-yl)-3-[4-(piperidin-1-yl)phen-yl]prop-2-en-1-one, C28H25NO, (I), and (E)-1-(anthracen-9-yl)-3-[4-(di-phenyl-amino)-phen-yl]prop-2-en-1-one, C35H25NO, (II), with the fused-ring system at the same position are described. In the crystals of (I) and (II), the mol-ecules are linked via C-H⋯O hydrogen bonds into inversion dimers, forming R22(22) and R22(14) ring motifs, respectively. Weak inter-molecular C-H⋯π inter-actions further help to stabilize the crystal structure, forming a two-dimensional architecture. The mol-ecular structures are optimized using density functional theory (DFT) at B3LYP/6-311 G++(d,p) level and compared with the experimental results. The smallest HOMO-LUMO energy gaps of (I) (exp . 2.76 eV and DFT 3.40 eV) and (II) (exp . 2.70 eV and DFT 3.28 eV) indicates the suitability of these crystals in optoelectronic applications. All inter-molecular contacts and weaker contributions involved in the supra-molecular stabilization are investigated using Hirshfeld surface analysis. The mol-ecular electrostatic potential (MEP) further identifies the positive, negative and neutral electrostatic potential regions of the mol-ecules.
Highlights
Chalcone derivatives have attracted significant attention in the past few decades mainly because of their availability of high optical non-linearities resulting from the significant delocalization of the electron clouds throughout the chalcone system (D’silva et al, 2011)
The torsion angle difference between the experimental and density functional theory (DFT) studies are due to the formation of intermolecular interactions involving the anthracene fusedring system and the terminal substituent of the 1-phenylpiperidine and triphenylamine units
The calculations of the molecular orbital geometry show that the absorption maxima of the molecules correspond to the electron transition between the frontier orbitals highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) (Fig. 5)
Summary
Chalcone derivatives have attracted significant attention in the past few decades mainly because of their availability of high optical non-linearities resulting from the significant delocalization of the electron clouds throughout the chalcone system (D’silva et al, 2011). A chalcone molecule with a -conjugated system provides a large charge-transfer axis with appropriate substituent groups on the two aromatic terminal rings. -conjugated molecular materials with fused rings are the focus of considerable interest in the emerging area of organic electronics, since the combination of excellent charge-carrier mobility and a high stability structure leads to potential optoelectronic applications (Wu et al, 2010). As part of our studies in this area, the chalcone compounds (E)-1(anthracen-9-yl)-3-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one, (I), and (E)-1-(anthracen-9-yl)-3-[4-(diphenylamino)phenyl]prop-2-en-1-one, (II), were successfully synthesized and their crystal structures are reported
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