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Quinolines by three-component reaction : synthesis and photophysical studies

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Quinolines by three-component reaction : synthesis and photophysical studies

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Título Quinolines by three-component reaction : synthesis and photophysical studies
Autor Sales, Eric Souza
Schneider, Juliana Maria Forain Miolo
Santos, Marcos José Leite
Bortoluzzi, Adailton João
Cardoso, Daniel Rodrigues
Santos, Willy Glen
Merlo, Aloir Antonio
Abstract The synthesis of five quinolines 8-octyloxy-4-[4-(octyloxy)phenyl]quinoline and 6-alkoxy- 2-(4-alkoxyphenyl)-4-[(4-octyloxy)aryl]quinolines are described by three-component coupling reaction mediated by Lewis acid FeCl3 and Yb(OTf)3. 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 π,π* and n,π* transitions. No changes were observed to lower-energy absorption band (e < 104 mol L-1 cm-1) related to n,π* 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 ms 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.
Contido em Journal of the Chemical Society. Vol. 26, n. 3 (mar. 2015), p. 562-571
Assunto Cristais
Fotofísica
Fotólise
Microscopia otica
Quinolinas
[en] Flash photolysis
[en] Photophysics
[en] Quinolines
[en] Single-crystal resolution
[en] Three-component synthesis
Origem Estrangeiro
Tipo Artigo de periódico
URI http://hdl.handle.net/10183/148872
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