Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas
Ano de defesa: | 2020 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/23965 |
Resumo: | The present work describes the synthesis, structural study and evaluation of the photophysical properties of new Schiff bases, (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols, as well as their application in the construction of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluormethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine. Structural and electronic properties were investigated by 1H, 13C, 19F NMR and by single-crystal X-ray diffraction. Initially, a series of (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols (10-14), obtained from reactions between 4-(trifluormethyl)quinolin-6-amines (4a-f) and substituted salicylaldehydes (5-9), in yields of 20-91%. In sequence, the photophysical properties of absorption, emission, quantum fluorescence yield, Stokes displacement, photostability and singlet oxygen quantum yield assays of Schiff bases 10-14 were evaluated. Subsequently, the Schiff's bases (10-14) were subjected to an imine function reduction reaction using NaBH4 as a reducing agent, leading to the formation of an unprecedented series of 2-(((2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)amino)methyl)phenols (15-19) in yields of 51-98%. Finally, the amines originated 15-19 were used, in the presence of formaldehyde (20) in Mannich type cyclization reactions in the synthesis of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3] oxazine (21-25), in yields of 50-95%. |
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2022-03-28T18:31:58Z2022-03-28T18:31:58Z2020-09-24http://repositorio.ufsm.br/handle/1/23965The present work describes the synthesis, structural study and evaluation of the photophysical properties of new Schiff bases, (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols, as well as their application in the construction of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluormethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine. Structural and electronic properties were investigated by 1H, 13C, 19F NMR and by single-crystal X-ray diffraction. Initially, a series of (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols (10-14), obtained from reactions between 4-(trifluormethyl)quinolin-6-amines (4a-f) and substituted salicylaldehydes (5-9), in yields of 20-91%. In sequence, the photophysical properties of absorption, emission, quantum fluorescence yield, Stokes displacement, photostability and singlet oxygen quantum yield assays of Schiff bases 10-14 were evaluated. Subsequently, the Schiff's bases (10-14) were subjected to an imine function reduction reaction using NaBH4 as a reducing agent, leading to the formation of an unprecedented series of 2-(((2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)amino)methyl)phenols (15-19) in yields of 51-98%. Finally, the amines originated 15-19 were used, in the presence of formaldehyde (20) in Mannich type cyclization reactions in the synthesis of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3] oxazine (21-25), in yields of 50-95%.O presente trabalho descreve a síntese, o estudo estrutural e avaliação das propriedades fotofísicas de novas bases de Schiff, denominadas (E)-2-(((2-(alquil/aril/heteroaril)-4-(trifluormetil)quinolin-6-il)imino)metil)fenois, além da posterior aplicação na construção de sistemas inéditos 3-(2-(alquil/aril/heteroaril)-4-(trifluormetil)quinolin-6-il)-3,4-diidro-2H-benzo[e][1,3]oxazina. As elucidações estruturais foram obtidas por RMN de 1H, 13C, 19F e difração de raios X em monocristral. Inicialmente foram obtidas uma série de (E)-2-(((2-(alquil/aril/heteroaril)-4-(trifluormetil)quinolin-6-il)imino)metil)fenois (10-14), obtidas a partir de reações entre 4-(trifluormetil)quinolin-6-aminas (4a-f) e salicilaldeídos substituídos (5-9), com rendimentos de 20-92%. Em sequência, foram avaliadas as propriedades fotofísicas de absorção, emissão, rendimento quântico de fluorescência, deslocamento de Stokes, ensaios de fotoestabilidade e rendimento quântico de oxigênio singlete das bases de Schiff 10-14. Posteriormente, as bases de Schiff (10-14) foram submetidas a reação de redução da função imina utilizando NaBH4 como agente redutor, levando a formação de uma série inédita de 2-(((2-(alquil/aril/heteroaril)-4-(trifluormetil)quinolin-6-il)amino)metil)fenois (15-19) em rendimentos de 51-98%. Finalmente, as aminas originadas 15-19 foram empregadas, na presença de formaldeído (20) em reações de ciclização do tipo Mannich na síntese de sistemas inéditos 3-(2-(alquil/aril/heteroaril)-4-(trifluormetil)quinolin-6-il)-3,4-diidro-2H-benzo[e][1,3] oxazina (21-25), com rendimentos de 50-95%.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessBases de SchiffBenzoxazinasPropriedades fotofísicasSchiff basesBenzoxazinePhotophysical propertiesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinasSynthesis and photophysical properties of schiff and 1,3-benzoxazines derived from 6-amino-4-(trifluormetyl) quinolinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Zanatta, NiloIglesias, Bernardo AlmeidaSevero Filho, Wolmar Alipiohttp://lattes.cnpq.br/3818799282351192Rocha, Inaiá Oliveira da10060000000060060060060060060006c852ad-d805-43c3-99d6-93a6a86f507cd87dcdee-07be-4650-926f-9424c67e8381798773ff-ec37-46f0-b925-27d7c30a6c20483d6d0c-e419-454b-b413-1a51673258c3b563f0d5-9d31-44d4-b811-4754bb0eac16reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMLICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/23965/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53ORIGINALDIS_PPGQUÍMICA_2020_ROCHA_INAIÁ.pdfDIS_PPGQUÍMICA_2020_ROCHA_INAIÁ.pdfDissertação de mestradoapplication/pdf18811840http://repositorio.ufsm.br/bitstream/1/23965/1/DIS_PPGQU%c3%8dMICA_2020_ROCHA_INAI%c3%81.pdf5df0828d84b8f2c881f9b10bdb1e716aMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/23965/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD521/239652022-03-28 15:31:58.193oai:repositorio.ufsm.br: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 Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-03-28T18:31:58Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
dc.title.alternative.eng.fl_str_mv |
Synthesis and photophysical properties of schiff and 1,3-benzoxazines derived from 6-amino-4-(trifluormetyl) quinolines |
title |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
spellingShingle |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas Rocha, Inaiá Oliveira da Bases de Schiff Benzoxazinas Propriedades fotofísicas Schiff bases Benzoxazine Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
title_full |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
title_fullStr |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
title_full_unstemmed |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
title_sort |
Síntese e propriedades fotofísicas de bases de schiff e 1,3-benzoxazinas derivadas de 6-amino-4-(trifluormetil)quinolinas |
author |
Rocha, Inaiá Oliveira da |
author_facet |
Rocha, Inaiá Oliveira da |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.advisor-co1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee1.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee2.fl_str_mv |
Severo Filho, Wolmar Alipio |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3818799282351192 |
dc.contributor.author.fl_str_mv |
Rocha, Inaiá Oliveira da |
contributor_str_mv |
Bonacorso, Helio Gauze Zanatta, Nilo Iglesias, Bernardo Almeida Severo Filho, Wolmar Alipio |
dc.subject.por.fl_str_mv |
Bases de Schiff Benzoxazinas Propriedades fotofísicas |
topic |
Bases de Schiff Benzoxazinas Propriedades fotofísicas Schiff bases Benzoxazine Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Schiff bases Benzoxazine Photophysical properties |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present work describes the synthesis, structural study and evaluation of the photophysical properties of new Schiff bases, (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols, as well as their application in the construction of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluormethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine. Structural and electronic properties were investigated by 1H, 13C, 19F NMR and by single-crystal X-ray diffraction. Initially, a series of (E)-2-(((2-(alkyl/aryl/heteroaryl)-4-trifluormethyl)quinolin-6-il)imino)methyl)phenols (10-14), obtained from reactions between 4-(trifluormethyl)quinolin-6-amines (4a-f) and substituted salicylaldehydes (5-9), in yields of 20-91%. In sequence, the photophysical properties of absorption, emission, quantum fluorescence yield, Stokes displacement, photostability and singlet oxygen quantum yield assays of Schiff bases 10-14 were evaluated. Subsequently, the Schiff's bases (10-14) were subjected to an imine function reduction reaction using NaBH4 as a reducing agent, leading to the formation of an unprecedented series of 2-(((2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)amino)methyl)phenols (15-19) in yields of 51-98%. Finally, the amines originated 15-19 were used, in the presence of formaldehyde (20) in Mannich type cyclization reactions in the synthesis of novel systems 3-(2-(alkyl/aryl/heteroaryl)-4-(trifluoromethyl)quinolin-6-yl)-3,4-dihydro-2H-benzo[e][1,3] oxazine (21-25), in yields of 50-95%. |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-09-24 |
dc.date.accessioned.fl_str_mv |
2022-03-28T18:31:58Z |
dc.date.available.fl_str_mv |
2022-03-28T18:31:58Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/23965 |
url |
http://repositorio.ufsm.br/handle/1/23965 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
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