Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/23963 |
Resumo: | The present work describes the synthesis, structural study and evaluation of the photophysical properties of a series of eight 1,3,5-triaryl-substituted 2-pyrazolin derivatives, as well as their application in obtaining a novel series of 2-(1,5-aryl-1H-pyrazol-3-yl)-phenol-1H-1,2,3-triazoles, 3-aryl = 2-OH-C6H4 and 5-aryl = Ph, 1-Naphthyl, 4-Br-C6H4, 4-F-C6H4, 4-OCH3-C6H4, 4-NO2-C6H4, 4-(N(CH3)2)-C6H4. The structural and electronic properties were investigated by high resolution mass spectrometry (HRMS), 1H, 13C and 19F NMR and by single crystal X-ray diffraction. The proposed methodology started with the synthesis of 2-pyrazoline precursors, called 2-(1,5-aryl-1H-pyrazol-3-yl)-phenols (5), obtained from cyclocondensation [3 + 2] between phenylhydrazine 4 and α,β-insaturated ketones, where, in this work, chalcones (3) were used which were synthesized by employing ortho-hydroxyacetophenone (1) and substituted benzaldehydes (2), in yields of 40-78%. Subsequently, the 2-pyrazolin derivatives 5 were subjected to evaluation of their photophysical properties of absorption, emission, fluorescence quantum yield and Stokes shift evaluated and correlated to theoretical calculations (TD-DFT) for the verification of the ESIPT phenomenon. The UV-Vis absorption properties of the 2-pyrazoline derivatives were evaluated in DCM, MeCN, AcOEt, EtOH, and DMSO as solvents and showed a fluorescence shift to the polar aprotic solvents, emitting a band in the blue region when excited at the least energetic transition of each compound. Furthermore, the 2-pyrazoline derivatives showed similar absorption and emission properties in the solid state with the previously mentioned in-solution assays. With the theoretical TD-DFT (Density Functional Theory) calculations performed, it was possible to observe that all compounds showed electronic density throughout the pyrazoline ring. Noteworthy, that by the LUMO orbital analysis, only the derivatives 5c (4-NO2-C6H4) and 5f (1-Naphthyl) exhibited the electronic density located in the portion of the molecule where the substituents were. In sequence, the 2-pyrazoline compounds 5 were precursors for the synthesis of 1,5-aryl-3-(2-(prop-2-in-1-yloxy) phenyl)-4,5-dihydro-1H-pyrazole 7 using propargyl bromide (6) as O-alkylating agent in obtaining terminal alkynes, via SN2-type reactions, in yields of 41-71%. Finally, the synthesized propargyl ethers 7 were employed in regioselective 1,3-dipolar cycloaddition reactions catalyzed by copper salts (CuAAC - Click Chemistry) with benzyl azide (8) to obtain 1H-1,2,3-triazolyl-pyrazolin 1,3,5-triaryl-substituted systems (9) in yields of 30-51%, being represented by five synthetic specimens. |
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2022-03-28T18:00:55Z2022-03-28T18:00:55Z2021-11-26http://repositorio.ufsm.br/handle/1/23963The present work describes the synthesis, structural study and evaluation of the photophysical properties of a series of eight 1,3,5-triaryl-substituted 2-pyrazolin derivatives, as well as their application in obtaining a novel series of 2-(1,5-aryl-1H-pyrazol-3-yl)-phenol-1H-1,2,3-triazoles, 3-aryl = 2-OH-C6H4 and 5-aryl = Ph, 1-Naphthyl, 4-Br-C6H4, 4-F-C6H4, 4-OCH3-C6H4, 4-NO2-C6H4, 4-(N(CH3)2)-C6H4. The structural and electronic properties were investigated by high resolution mass spectrometry (HRMS), 1H, 13C and 19F NMR and by single crystal X-ray diffraction. The proposed methodology started with the synthesis of 2-pyrazoline precursors, called 2-(1,5-aryl-1H-pyrazol-3-yl)-phenols (5), obtained from cyclocondensation [3 + 2] between phenylhydrazine 4 and α,β-insaturated ketones, where, in this work, chalcones (3) were used which were synthesized by employing ortho-hydroxyacetophenone (1) and substituted benzaldehydes (2), in yields of 40-78%. Subsequently, the 2-pyrazolin derivatives 5 were subjected to evaluation of their photophysical properties of absorption, emission, fluorescence quantum yield and Stokes shift evaluated and correlated to theoretical calculations (TD-DFT) for the verification of the ESIPT phenomenon. The UV-Vis absorption properties of the 2-pyrazoline derivatives were evaluated in DCM, MeCN, AcOEt, EtOH, and DMSO as solvents and showed a fluorescence shift to the polar aprotic solvents, emitting a band in the blue region when excited at the least energetic transition of each compound. Furthermore, the 2-pyrazoline derivatives showed similar absorption and emission properties in the solid state with the previously mentioned in-solution assays. With the theoretical TD-DFT (Density Functional Theory) calculations performed, it was possible to observe that all compounds showed electronic density throughout the pyrazoline ring. Noteworthy, that by the LUMO orbital analysis, only the derivatives 5c (4-NO2-C6H4) and 5f (1-Naphthyl) exhibited the electronic density located in the portion of the molecule where the substituents were. In sequence, the 2-pyrazoline compounds 5 were precursors for the synthesis of 1,5-aryl-3-(2-(prop-2-in-1-yloxy) phenyl)-4,5-dihydro-1H-pyrazole 7 using propargyl bromide (6) as O-alkylating agent in obtaining terminal alkynes, via SN2-type reactions, in yields of 41-71%. Finally, the synthesized propargyl ethers 7 were employed in regioselective 1,3-dipolar cycloaddition reactions catalyzed by copper salts (CuAAC - Click Chemistry) with benzyl azide (8) to obtain 1H-1,2,3-triazolyl-pyrazolin 1,3,5-triaryl-substituted systems (9) in yields of 30-51%, being represented by five synthetic specimens.O presente trabalho descreve a síntese, o estudo estrutural e a avaliação das propriedades fotofísicas de uma série de oito derivados 2-pirazolínicos 1,3,5-triaril-substituídos, além da aplicação destes na obtenção de uma série inédita de 2-(1,5-aril-1H-pirazol-3-il)-fenol-1H-1,2,3-triazóis, sendo 3-aril = 2-OH-C6H4 e 5-aril = Ph, 1-Naftil, 4-Br-C6H4, 4-F-C6H4, 4-OCH3-C6H4, 4-NO2-C6H4, 4-(N(CH3)2)-C6H4. As propriedades estruturais e eletrônicas foram investigadas por espectrometria de massas de alta resolução (HRMS), RMN de 1H, 13C e 19F e por difração de raios X em monocristal. A metodologia proposta iniciou com a síntese dos precursores 2-pirazolínicos, denominados 2-(1,5-aril-1H-pirazol-3-il)-fenóis (5), obtidos a partir ciclocondensação [3 + 2] entre fenilhidrazina 4 e cetonas α,β-insaturadas, em que, neste trabalho, utilizaram-se as chalconas (3) que foram sintetizadas empregando a orto-hidróxi-acetofenona (1) e benzaldeídos substituídos (2), em rendimentos de 40-78%. Posteriormente, os derivados 2-pirazolinícos 5 foram submetidos a avaliação de suas propriedades fotofísicas de absorção, emissão, rendimento quântico de fluorescência e deslocamento de Stokes avaliadas e correlacionadas a cálculos teóricos (TD-DFT) para a verificação do fenômeno ESIPT. As propriedades de absorção UV-Vis dos derivados 2-pirazolínicos foram avaliadas em DCM, MeCN, AcOEt, EtOH, e DMSO como solvente e apresentaram uma mudança de fluorescência para os solventes polares apróticos, emitindo uma banda na região azul quando excitados na transição menos energética de cada composto. Além disso, os derivados 2-pirazolínicos apresentaram propriedades de absorção e emissão no estado sólido semelhantes com os ensaios em solução anteriormente mencionados. Com os cálculos teóricos TD-DFT (Teoria do Funcional Densidade) realizados, foi possível observar que todos os compostos apresentaram densidade eletrônica em todo o anel pirazolínico. Destaca-se, que pela análise do orbital LUMO, apenas os derivados 5c (4-NO2-C6H4) e 5f (1-Naftil) exibiram a densidade eletrônica localizada na porção da molécula onde encontravam-se os substituintes. Em sequência, os compostos 2-pirazolínicos 5 foram precursores para a síntese de 1,5-aril-3-(2-(prop-2-in-1-iloxi) fenil)-4,5-diidro-1H-pirazol 7 utilizando brometo de propargila (6) como O-alquilante na obtenção de alcinos terminais, via reações do tipo SN2, com rendimentos de 41-71%. Finalmente, os éteres propargílicos 7 sintetizados foram empregados em reações de cicloadição 1,3-dipolares regiosseletivas catalisadas por sais de cobre (CuAAC - Click Chemistry) com benzil azida (8) para a obtenção de sistemas 1H-1,2,3-triazolil-pirazolínicos 1,3,5-triaril-substituídos (9) com rendimentos de 30-51%, sendo representados por cinco exemplares sintéticos.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccess2-pirazolínicos1,2,3-triazóisPropriedades fotofísicasESIPT2-pyrazolines1,2,3-triazolesPhotophysical propertiesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivadosSynthesis and photophysical properties of 2-(5-aryl-4,5-dihydro-1H-1-phenylpyrazol-3-yl) phenols and derived pyrazolyl-triazole systemsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Iglesias, Bernardo AlmeidaSevero, Wolmarhttp://lattes.cnpq.br/7208565749396153Santos, Gabriel da Costa100600000000600600600600600f7323eee-b707-444a-a969-1a044768188a88bc524a-073c-441a-837d-39a35c8911f5483d6d0c-e419-454b-b413-1a51673258c3f8a8d9c6-e958-4cb6-a448-a1a0758b6cd6reponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
dc.title.alternative.eng.fl_str_mv |
Synthesis and photophysical properties of 2-(5-aryl-4,5-dihydro-1H-1-phenylpyrazol-3-yl) phenols and derived pyrazolyl-triazole systems |
title |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
spellingShingle |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados Santos, Gabriel da Costa 2-pirazolínicos 1,2,3-triazóis Propriedades fotofísicas ESIPT 2-pyrazolines 1,2,3-triazoles Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
title_full |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
title_fullStr |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
title_full_unstemmed |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
title_sort |
Síntese e propriedades fotofísicas de 2-(5-aril-4,5-diidro-1H-1-fenilpirazol-3-il) fenóis e sistemas pirazolil-triazólicos derivados |
author |
Santos, Gabriel da Costa |
author_facet |
Santos, Gabriel da Costa |
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.referee1.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee2.fl_str_mv |
Severo, Wolmar |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7208565749396153 |
dc.contributor.author.fl_str_mv |
Santos, Gabriel da Costa |
contributor_str_mv |
Bonacorso, Helio Gauze Iglesias, Bernardo Almeida Severo, Wolmar |
dc.subject.por.fl_str_mv |
2-pirazolínicos 1,2,3-triazóis Propriedades fotofísicas ESIPT |
topic |
2-pirazolínicos 1,2,3-triazóis Propriedades fotofísicas ESIPT 2-pyrazolines 1,2,3-triazoles Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
2-pyrazolines 1,2,3-triazoles 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 a series of eight 1,3,5-triaryl-substituted 2-pyrazolin derivatives, as well as their application in obtaining a novel series of 2-(1,5-aryl-1H-pyrazol-3-yl)-phenol-1H-1,2,3-triazoles, 3-aryl = 2-OH-C6H4 and 5-aryl = Ph, 1-Naphthyl, 4-Br-C6H4, 4-F-C6H4, 4-OCH3-C6H4, 4-NO2-C6H4, 4-(N(CH3)2)-C6H4. The structural and electronic properties were investigated by high resolution mass spectrometry (HRMS), 1H, 13C and 19F NMR and by single crystal X-ray diffraction. The proposed methodology started with the synthesis of 2-pyrazoline precursors, called 2-(1,5-aryl-1H-pyrazol-3-yl)-phenols (5), obtained from cyclocondensation [3 + 2] between phenylhydrazine 4 and α,β-insaturated ketones, where, in this work, chalcones (3) were used which were synthesized by employing ortho-hydroxyacetophenone (1) and substituted benzaldehydes (2), in yields of 40-78%. Subsequently, the 2-pyrazolin derivatives 5 were subjected to evaluation of their photophysical properties of absorption, emission, fluorescence quantum yield and Stokes shift evaluated and correlated to theoretical calculations (TD-DFT) for the verification of the ESIPT phenomenon. The UV-Vis absorption properties of the 2-pyrazoline derivatives were evaluated in DCM, MeCN, AcOEt, EtOH, and DMSO as solvents and showed a fluorescence shift to the polar aprotic solvents, emitting a band in the blue region when excited at the least energetic transition of each compound. Furthermore, the 2-pyrazoline derivatives showed similar absorption and emission properties in the solid state with the previously mentioned in-solution assays. With the theoretical TD-DFT (Density Functional Theory) calculations performed, it was possible to observe that all compounds showed electronic density throughout the pyrazoline ring. Noteworthy, that by the LUMO orbital analysis, only the derivatives 5c (4-NO2-C6H4) and 5f (1-Naphthyl) exhibited the electronic density located in the portion of the molecule where the substituents were. In sequence, the 2-pyrazoline compounds 5 were precursors for the synthesis of 1,5-aryl-3-(2-(prop-2-in-1-yloxy) phenyl)-4,5-dihydro-1H-pyrazole 7 using propargyl bromide (6) as O-alkylating agent in obtaining terminal alkynes, via SN2-type reactions, in yields of 41-71%. Finally, the synthesized propargyl ethers 7 were employed in regioselective 1,3-dipolar cycloaddition reactions catalyzed by copper salts (CuAAC - Click Chemistry) with benzyl azide (8) to obtain 1H-1,2,3-triazolyl-pyrazolin 1,3,5-triaryl-substituted systems (9) in yields of 30-51%, being represented by five synthetic specimens. |
publishDate |
2021 |
dc.date.issued.fl_str_mv |
2021-11-26 |
dc.date.accessioned.fl_str_mv |
2022-03-28T18:00:55Z |
dc.date.available.fl_str_mv |
2022-03-28T18:00:55Z |
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/1/23963 |
url |
http://repositorio.ufsm.br/handle/1/23963 |
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 |
dc.relation.authority.fl_str_mv |
f7323eee-b707-444a-a969-1a044768188a 88bc524a-073c-441a-837d-39a35c8911f5 483d6d0c-e419-454b-b413-1a51673258c3 f8a8d9c6-e958-4cb6-a448-a1a0758b6cd6 |
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 |
reponame:Repositório Institucional Manancial UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Repositório Institucional Manancial UFSM |
collection |
Repositório Institucional Manancial UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/23963/2/license_rdf http://repositorio.ufsm.br/bitstream/1/23963/3/license.txt http://repositorio.ufsm.br/bitstream/1/23963/1/DIS_PPGQU%c3%8dMICA_2021_SANTOS_GABRIEL.pdf |
bitstream.checksum.fl_str_mv |
4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df 4ad9b54568bcdd666d37f49fdf091537 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
ouvidoria@ufsm.br |
_version_ |
1808854723282862080 |