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Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT study

Khalid, Muhammad ; Ullah, Malik Aman ; Adeel, Muhammad ; Usman Khan, Muhammad ; Tahir, Muhammad Nawaz ; Braga, Ataualpa Albert Carmo

Journal of Saudi Chemical Society, 2019-07, Vol.23 (5), p.546-560 [Periódico revisado por pares]

Elsevier B.V

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  • Título:
    Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT study
  • Autor: Khalid, Muhammad ; Ullah, Malik Aman ; Adeel, Muhammad ; Usman Khan, Muhammad ; Tahir, Muhammad Nawaz ; Braga, Ataualpa Albert Carmo
  • Assuntos: 3-Arylated quinolines ; Crystal structures ; Density functional theory ; Nonlinear optical properties ; Spectroscopic data ; Suzuki–Miyaura cross-coupling
  • É parte de: Journal of Saudi Chemical Society, 2019-07, Vol.23 (5), p.546-560
  • Descrição: [Display omitted] •Three novel arylated quinolines were synthesized employing Pd catalyzed Suzuki–Miyaura cross-coupling reaction.•XRD, NMR, FT-IR, UV–Vis, EIMS and elemental analysis were performed for the characterization.•Computational study at B3LYP/6-311+G(2d,p) level reveals a good agreement with experimental results.•Frontier molecular orbital and natural bond orbital analysis were performed.•Nonlinear optical properties were calculated and confirmed using two-state model. Quinoline and its derivatives are widely studied by both synthetic and computational chemists due to their exciting perspectives in biological and nonlinear optical (NLO) research. Herein, three novel arylated quinolines: 3-(4-acetylphenyl)quinoline (1), 3-(4-(methylthio)phenyl)-quinoline (2) and 3-(4-phenoxyphenyl)quinoline (3) were synthesized employing Pd catalyzed Suzuki–Miyaura cross-coupling reaction. The chemical structures of all compounds were resolved employing different analytical techniques like 1H-NMR, FT-IR, UV–Vis, EIMS, elemental analysis and finally confirmed by single crystal X-ray diffraction analysis. Synthesized compounds were further subjected to density functional theory (DFT) calculations at B3LYP level of theory in conjunction with 6-311 + G(2d,p) basis set to explore optimized geometry, natural bond orbital (NBO) analysis, FT-IR spectroscopic data, frontier molecular orbitals (FMOs) and NLO properties. Overall, a good agreement was found between DFT computed results and corresponding experimental findings. Vertical electronic transition states were computationally calculated using time-dependent DFT (TDDFT) at same B3LYP level of theory and 6-311 + G(2d,p) basis set combination. NBO calculations indicated the occurrence of intra-molecular charge transfer in synthesized compounds, hence enormous molecular stability owing to hyperconjugative interactions. Energy of FMOs was used to calculate the global reactivity descriptors which indicated that synthesized molecules are chemically hard compounds with greater kinetic stability and electron donating capability. NLO properties were found to be in the range 1830–2960 a.u and order of 2 > 1 > 3. Urea molecule comparative analysis and two-state model confirmed that synthesized molecules are excellent NLO candidates and may have prospective uses in the technology related applications.
  • Editor: Elsevier B.V
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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