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Effect of the substituents of new coumarin-imidazo[1,2-a]heterocyclic-3-acrylate derivatives on nonlinear optical properties: a combined experimental-theoretical approach.
Vázquez, Juan Luis; Velazco-Cabral, Iván; Alvarado-Méndez, Edgar; Trejo-Durán, Mónica; Flores-Alamo, Marcos; Peña-Cabrera, Eduardo; García-Revilla, Marco A; Vázquez, Miguel A.
Afiliação
  • Vázquez JL; Chemistry Department, DCNE, University of Guanajuato, Noria Alta s/n, 36050, Guanajuato, Gto, Mexico. mvazquez@ugto.mx.
  • Velazco-Cabral I; Chemistry Department, DCNE, University of Guanajuato, Noria Alta s/n, 36050, Guanajuato, Gto, Mexico. mvazquez@ugto.mx.
  • Alvarado-Méndez E; Engineering Division Campus Irapuato-Salamanca, University of Guanajuato, Palo Blanco s/n, 36885, Salamanca, Gto, Mexico.
  • Trejo-Durán M; Engineering Division Campus Irapuato-Salamanca, University of Guanajuato, Palo Blanco s/n, 36885, Salamanca, Gto, Mexico.
  • Flores-Alamo M; Faculty of Chemistry, National Autonomous University of Mexico, Av. Insurgentes Sur S/N, 04510, DF, Mexico.
  • Peña-Cabrera E; Chemistry Department, DCNE, University of Guanajuato, Noria Alta s/n, 36050, Guanajuato, Gto, Mexico. mvazquez@ugto.mx.
  • García-Revilla MA; Chemistry Department, DCNE, University of Guanajuato, Noria Alta s/n, 36050, Guanajuato, Gto, Mexico. mvazquez@ugto.mx.
  • Vázquez MA; Chemistry Department, DCNE, University of Guanajuato, Noria Alta s/n, 36050, Guanajuato, Gto, Mexico. mvazquez@ugto.mx.
Phys Chem Chem Phys ; 23(39): 22466-22475, 2021 Oct 13.
Article em En | MEDLINE | ID: mdl-34585696
A series of new coumarin-imidazo[1,2-a]heterocyclic-3-acrylate derivatives 7a-h were synthesized by the Heck reaction between the corresponding 3-(imidazo[1,2-a]pyrimidines)-(2-yl)-2H-chromen-2-ones 4a-e and methyl acrylate in 45-87% yields. The effect of the distinct substituents on third-order nonlinear optical properties was examined, experimentally measuring their nonlinear refractive indexes by the Z-scan technique. Density functional theory and time-dependent density functional theory were utilized with the B3LYP, CAM-B3LYP, PBE (PBEPBE), and M062X functionals on Gaussian09 software to calculate the vertical excitation, relaxation of the brightest excited states, conformation, HOMO-LUMO gaps, oscillator strength, polarizability, and hyperpolarizabilities of all derivatives. Although all acrylates showed a nonlinear response at a certain level of power, the compounds bearing a diethylamino electron-donating group exhibited higher nonlinear refractive index values (∼10-9 cm2 W-1), which is in agreement with the trend in the computational calculations of the first and second hyperpolarization. According to the structural analysis, the electron-withdrawing group (acrylate) is mainly responsible for the loss of coplanarity because of increasing the dihedral angle between the coumarin and imidazo[1,2-a]heterocyclic moieties (to 39.1°). On the other hand, the unsubstituted compound 4a presented the greatest nonlinearity due to its almost coplanar structure (n2 ∼ 10-8 cm2 W-1), highlighting the importance of this feature.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Phys Chem Chem Phys Assunto da revista: BIOFISICA / QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: México País de publicação: Reino Unido
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Phys Chem Chem Phys Assunto da revista: BIOFISICA / QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: México País de publicação: Reino Unido