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

Acta Crystallographica. Section E, Crystallographic Communications
Dian Alwani ZainuriSuhana Arshad

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⋯π 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.

References

Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Mar 26, 2008·Chemical Society Reviews·Marta Mas-Torrent, Concepció Rovira
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Jul 1, 2011·The Journal of Organic Chemistry·Jon P NietfeldSeth C Rasmussen
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jun 2, 2015·Acta Crystallographica. Section E, Crystallographic Communications·Aditya AgrahariWiley J Youngs
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Jun 17, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Amzar Ahlami AbdullahIbrahim Abdul Razak
Aug 19, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Marisiddaiah GirishaChristopher Glidewell
May 17, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Dian Alwani ZainuriSuhana Arshad

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Citations

May 22, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Muhamad Fikri ZainiSuhana Arshad
Jun 29, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Dian Alwani ZainuriSuhana Arshad
Oct 16, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Dian Alwani ZainuriSuhana Arshad
Oct 16, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Dian Alwani ZainuriSuhana Arshad

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Methods Mentioned

BETA
X-ray

Software Mentioned

Gaussian09

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