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(es)

Khalid, Muhammad ^[1] ; Ullah, Malik Aman ^[2] ; Adeel, Muhammad ^[2] ; Khan, Muhammad Usman ^[3] ; Tahir, Uhammad Nawaz ^[4] ; Carmo Braga, Ataualpa Albert ^[5]

Afiliação do(s) autor(es)

^[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[2] Gomal Univ, Inst Chem Sci, Dera Ismail Khan 29050 - Pakistan

^[3] Govt Coll Univ, Dept Appl Chem, Faisalabad 38000 - Pakistan

^[4] Univ Sargodha, Dept Phys, Sargodha 40100 - Pakistan

^[5] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Ave Prof Lineu Prestes 748, BR-05508000 Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF SAUDI CHEMICAL SOCIETY; v. 23, n. 5, p. 546-560, JUL 2019.
• Citações Web of Science: 11

Resumo

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 1 H-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. (C) 2018 King Saud University. Production and hosting by Elsevier B.V. (AU)

• Processo FAPESP: 15/01491-3 - Estudo teórico das reações de acoplamento-cruzado: catálise homogênea e heterogênea
• Beneficiário: Ataualpa Albert Carmo Braga
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 14/25770-6 - Novas fronteiras em reações de acoplamento cruzado mediadas por paládio: associando catálise enantiosseletiva, ativações C-H, novos materiais e reações em fluxo visando alta eficiência e sustentabilidade em processos sintéticos
• Beneficiário: Carlos Roque Duarte Correia
• Linha de fomento: Auxílio à Pesquisa - Temático