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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Quinolines by Three-Component Reaction: Synthesis and Photophysical Studies

Texto completo
Autor(es):
Sales, Eric S. [1] ; Schneider, Juliana M. F. M. [1] ; Santos, Marcos J. L. [1] ; Bortoluzzi, Adailton J. [2] ; Cardoso, Daniel R. [3] ; Santos, Willy G. [3] ; Merlo, Aloir A. [1]
Número total de Autores: 7
Afiliação do(s) autor(es):
[1] Univ Fed Rio Grande do Sul, Inst Quim, BR-90040060 Porto Alegre, RS - Brazil
[2] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC - Brazil
[3] Univ Sao Paulo, Chem Inst Sao Carlos, BR-13566590 Sao Carlos, SP - Brazil
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: Journal of the Brazilian Chemical Society; v. 26, n. 3, p. 562-571, MAR 2015.
Citações Web of Science: 7
Resumo

The synthesis of five quinolines 8-octyloxy-4-{[}4-(octyloxy) phenyl] quinoline and 6-alkoxy2-(4-alkoxyphenyl)-4-{[}(4-octyloxy) aryl] quinolines are described by three-component coupling reaction mediated by Lewis acid FeCl3 and Yb(OTf)(3)center dot 4-n-octyloxybenzaldehyde, anisaldehyde, 4-n-octyloxyaniline p-anisidine, and 1-ethynyl-4-heptyloxybenzene, 1-ethynyl-4-octyloxybenzene and 2-ethynyl-6-heptyloxynaphthalene are the reagents in this protocol. A Yb3+ catalyst resulted in higher yields of quinolines than Fe3+. Polarizing optical microscopy (POM) revealed that none of the quinolines were liquid crystals, even the more anisotropic. UV-Vis measurements of one of the quinolines in polar solvent show two absorption bands at 280 and 350 nm related to pi, pi{*} and n, pi{*} transitions. No changes were observed to lower-energy absorption band (epsilon < 10(4) mol L-1 cm(-1)) related to n, pi{*} transition. A laser flash photolysis study for one of the quinolines relates a main transient band at 450 nm with a lifetime of 2.6 mu s in ethanol, which is completely quenched in the presence of oxygen. This transient band was assigned to triplet-triplet absorption of one of the quinolines, which is semi-oxidised in the presence of phenol. Radiative rate constants have been determined along singlet and triplet excited state energies (3.39 and 3.10 eV, respectively). The chemical structure of one of the quinolines was also unequivocally confirmed by single-crystal X-ray analysis. (AU)

Processo FAPESP: 12/19823-4 - Fototransientes de organoboranos gerados por fotólise direta e sensitização por flavinas
Beneficiário:Willy Glen Santos
Linha de fomento: Bolsas no Brasil - Pós-Doutorado