Synthesis, structural characterization and computational study of a novel amino chalcone: a potential nonlinear optical material
dc.creator | Almeida, Leonardo Rodrigues de | |
dc.creator | Anjos, Murilo Machado dos | |
dc.creator | Ribeiro, Gabriela Cândido | |
dc.creator | Valverde, Clodoaldo | |
dc.creator | Machado, Daniel Francisco Scalabrini | |
dc.creator | Oliveira, Guilherme Roberto de | |
dc.creator | Napolitano, Hamilton Barbosa | |
dc.creator | Oliveira, Heibbe Cristhian Benedito de | |
dc.date.accessioned | 2024-01-25T15:02:52Z | |
dc.date.available | 2024-01-25T15:02:52Z | |
dc.date.issued | 2017 | |
dc.description.abstract | The interest for novel chalcone-based materials in nonlinear optics is dependent on strong second harmonic generation in organic systems. Chalcones are α,β-unsaturated ketones that can be easily obtained by Claisen–Schmidt condensation between ketones and aromatic aldehydes. A new 2-amino-chalcone was synthesized and its crystal molecular structure was elucidated using the single crystal X-ray diffraction technique. This compound, C15H12BrNO2, crystallizes in monoclinic centrosymmetric space group C2/c with cell parameters a = 29.47(7) Å; b = 6.97(5) Å, c = 13.59(1) Å, β = 112.52(6)° and V = 2581.2(2) Å3. In addition to the crystal structure, the analysis of Hirshfeld surfaces indicates the presence of hydrogen bonds of types N–H⋯O and O–H⋯O that stabilize two independent centrosymmetric dimers, and also indicates the presence of π–π stacking interactions that stabilize a supramolecular trimeric system. Being a push–pull chromophore we investigated the NLO properties of the 2-amino-chalcone asymmetric unit using the supermolecule approach in combination with an iterative electrostatic polarization scheme. The calculations were performed using the CAM-B3LYP/6-311+G(d) level of theory for both dynamic and static situations. In the presence of the embedding charges, the γ value is increased by 20% for the dynamic calculation but only 8% for the static limit. In contrast to the crystal form, when in solution the 2-amino-chalcone lacks an inversion center so that second order NLO properties do not vanish. Following this idea we computed the NLO properties using the implicit solvation approach IEF-PCM. The solvent effect on the NLO properties was to augment its values as the solvent polarity increases. We obtained for the in-crystal and in DMSO 2-amino-chalcone, γ(−2ω;ω,ω,0) = 144.12 × 10−36 esu and 260.163 × 10−36 esu, respectively, and therefore interesting materials for third order NLO applications. | |
dc.identifier.citation | ALMEIDA, Leonardo R. et al. Synthesis, structural characterization and computational study of a novel amino chalcone: a potential nonlinear optical material. New Journal of Chemistry, London, v. 41, n. 4, p. 1744-1754, 2017. DOI: 10.1039/C5NJ03214H. Disponível em: https://pubs.rsc.org/en/content/articlelanding/2017/NJ/C5NJ03214H. Acesso em: 14 dez. 2023. | |
dc.identifier.doi | 10.1039/C5NJ03214H | |
dc.identifier.issn | e- 1369-9261 | |
dc.identifier.uri | https://pubs.rsc.org/en/content/articlelanding/2017/NJ/C5NJ03214H | |
dc.language.iso | eng | |
dc.publisher.country | Gra-bretanha | |
dc.publisher.department | Instituto de Química - IQ (RMG) | |
dc.rights | Acesso Restrito | |
dc.title | Synthesis, structural characterization and computational study of a novel amino chalcone: a potential nonlinear optical material | |
dc.type | Artigo |
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