Quinolines by three-component reaction : synthesis and photophysical studies
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFRGS |
Texto Completo: | http://hdl.handle.net/10183/148872 |
Resumo: | 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. |
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Sales, Eric SouzaSchneider, Juliana Maria Forain MioloSantos, Marcos José LeiteBortoluzzi, Adailton JoãoCardoso, Daniel RodriguesSantos, Willy GlenMerlo, Aloir Antonio2016-10-06T02:14:20Z20150368-1769http://hdl.handle.net/10183/148872000999746The 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.application/pdfengJournal of the Chemical Society. Vol. 26, n. 3 (mar. 2015), p. 562-571QuinolinasFotofísicaFotóliseMicroscopia oticaCristaisQuinolinesThree-component synthesisSingle-crystal resolutionPhotophysicsFlash photolysisQuinolines by three-component reaction : synthesis and photophysical studiesEstrangeiroinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSORIGINAL000999746.pdf000999746.pdfTexto completo (inglês)application/pdf1961206http://www.lume.ufrgs.br/bitstream/10183/148872/1/000999746.pdf0b173b10e991680e6a5b25a98aaf48a4MD51TEXT000999746.pdf.txt000999746.pdf.txtExtracted Texttext/plain53445http://www.lume.ufrgs.br/bitstream/10183/148872/2/000999746.pdf.txt732a8ec9d2c76d95629b01615c3f9df7MD52THUMBNAIL000999746.pdf.jpg000999746.pdf.jpgGenerated Thumbnailimage/jpeg1797http://www.lume.ufrgs.br/bitstream/10183/148872/3/000999746.pdf.jpgb961fe05c4e144d2cfd7dadebb46a8aaMD5310183/1488722018-10-29 09:09:30.616oai:www.lume.ufrgs.br:10183/148872Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2018-10-29T12:09:30Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false |
dc.title.pt_BR.fl_str_mv |
Quinolines by three-component reaction : synthesis and photophysical studies |
title |
Quinolines by three-component reaction : synthesis and photophysical studies |
spellingShingle |
Quinolines by three-component reaction : synthesis and photophysical studies Sales, Eric Souza Quinolinas Fotofísica Fotólise Microscopia otica Cristais Quinolines Three-component synthesis Single-crystal resolution Photophysics Flash photolysis |
title_short |
Quinolines by three-component reaction : synthesis and photophysical studies |
title_full |
Quinolines by three-component reaction : synthesis and photophysical studies |
title_fullStr |
Quinolines by three-component reaction : synthesis and photophysical studies |
title_full_unstemmed |
Quinolines by three-component reaction : synthesis and photophysical studies |
title_sort |
Quinolines by three-component reaction : synthesis and photophysical studies |
author |
Sales, Eric Souza |
author_facet |
Sales, Eric Souza Schneider, Juliana Maria Forain Miolo Santos, Marcos José Leite Bortoluzzi, Adailton João Cardoso, Daniel Rodrigues Santos, Willy Glen Merlo, Aloir Antonio |
author_role |
author |
author2 |
Schneider, Juliana Maria Forain Miolo Santos, Marcos José Leite Bortoluzzi, Adailton João Cardoso, Daniel Rodrigues Santos, Willy Glen Merlo, Aloir Antonio |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Sales, Eric Souza Schneider, Juliana Maria Forain Miolo Santos, Marcos José Leite Bortoluzzi, Adailton João Cardoso, Daniel Rodrigues Santos, Willy Glen Merlo, Aloir Antonio |
dc.subject.por.fl_str_mv |
Quinolinas Fotofísica Fotólise Microscopia otica Cristais |
topic |
Quinolinas Fotofísica Fotólise Microscopia otica Cristais Quinolines Three-component synthesis Single-crystal resolution Photophysics Flash photolysis |
dc.subject.eng.fl_str_mv |
Quinolines Three-component synthesis Single-crystal resolution Photophysics Flash photolysis |
description |
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. |
publishDate |
2015 |
dc.date.issued.fl_str_mv |
2015 |
dc.date.accessioned.fl_str_mv |
2016-10-06T02:14:20Z |
dc.type.driver.fl_str_mv |
Estrangeiro info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
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format |
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publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10183/148872 |
dc.identifier.issn.pt_BR.fl_str_mv |
0368-1769 |
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000999746 |
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http://hdl.handle.net/10183/148872 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.pt_BR.fl_str_mv |
Journal of the Chemical Society. Vol. 26, n. 3 (mar. 2015), p. 562-571 |
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openAccess |
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