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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, C₂₅H₁₇NO, and (E)-1-(anthracen-9-yl)-3-[4-(di-methyl-amino)-naphthalen-1-yl]prop-2-en-1-one, C₂₉H₂₃NO, 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?? inter-actions 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 (inter-molecular charge transfers) of these systems.

SUBMITTER: Zainuri DA

PROVIDER: S-EPMC6176452 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Zainuri Dian Alwani DA Razak Ibrahim Abdul IA Arshad Suhana S

Acta crystallographica. Section E, Crystallographic communications 20180928 Pt 10

The crystal structures of (E)-1-(anthracen-9-yl)-3-(3H-indol-2-yl)prop-2-en-1-one, C25H17NO, and (E)-1-(anthracen-9-yl)-3-[4-(di-methyl-amino)-naphthalen-1-yl]prop-2-en-1-one, C29H23NO, 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 inter-actions ...[more]

PMID: 30319808

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Project description:In the present paper, the photophysical properties of metallocene-4-amino-1,8-naphthalimide-piperazine molecules (1-M2+), as well as their oxidized and protonated derivatives (1-M3+, 1-M2+-H+, and 1-M3+-H+), where M = Fe, Co, and Ni, were studied via DFT and TD-DFT, employing three functionals, i.e., PBE0, TPSSh, and wB97XD. The effect of the substitution of the transition metal M on their oxidation state, and/or the protonation of the molecules, was investigated. The present calculated systems have not been investigated before and, except for the data regarding their photophysical properties, the present study provides important information regarding the effect of geometry and of DFT methodology on absorption spectra. It was found that small differences in geometry, specifically in the geometry of N atoms, reflect significant differences in absorption spectra. The common differences in spectra due to the use of different functionals can be significantly increased when the functionals predict minima even with small geometry differences. For most of the calculated molecules, the main absorption peaks in visible and near-UV areas correspond mainly to charge transfer excitations. The Fe complexes present larger oxidation energies at 5.4 eV, whereas Co and Ni complexes have smaller ones, at about 3.5 eV. There are many intense UV absorption peaks with excitation energies similar to their oxidation energies, showing that the emission from these excited states can be antagonistic to their oxidation. Regarding the use of functionals, the inclusion of dispersion corrections does not affect the geometry, and consequently the absorption spectra, of the present calculated molecular systems. For certain applications, where there is a need for a redox molecular system including metallocene, the oxidation energies could be lowered significantly, to about 40%, with the replacement of the iron with cobalt or nickel. Finally, the present molecular system, using cobalt as the transition metal, has the potential to be used as a sensor.

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

Publications

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

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