Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/11789 |
Resumo: | In the chapter 1, studies on photocatalysed reactions were carried out by porphyrins and other photocatalysts aiming at the formation of radicals in amino aromatic systems for subsequent addition reaction. More specifically, double functionalization C-H reaction were studied by oxidative cyclization of N,N-dimethylaniline (16) with N-phenylmaleimide (17) to obtain tetrahydroquinolines, both by SET (single electron transfer) using meso-tetraphenylporphyrin (TPP) and Electron Donor-Acceptor (EDA) complex. For the evaluated reaction, the use of the photocatalyst TPP presented no influence on the formation of the product. Thus, experiments were additionally performed using N, N-dimethylaniline (16) and varying different electrophiles, however, it was not possible to observe the formation of the expected tetrahydroquinolines. Using the substrate fumaronitrile (65) gave a product of interest (2-(methyl(phenyl)amino)acetonitrile) (72), from a radical reaction of N,N-dimethylaniline (16) with fumaronitrile (65). Further, exploratory optimization experiments were performed, but unsuccesfully. Due to the appearance of related publications in the literature, it was decided to no longer insist on these studies. In the chapter 2 the synthesis and photophysical studies of hybrid molecules between curcumin (6) and bixin (11) were carried out aiming at the production of some new photosensitizing molecules for PDT applications. Curcumin is a compound well known by our research group with a well-established synthesis. Bixin (11) was extracted from the seeds of annatto by a modified methodology established in the literature. After obtaining these starting materials, the syntheses of chimeric photosensitizing molecules, the dimer (25) and the trimer (26) were studied. After the syntheses and characterizations of these compounds, studies of their photophysical properties were carried out, namely, studies of molar absorptivity, singlet oxygen quantum yield, photodegradation study, fluorescence quantum yield and aggregation. From these studies it was possible do stablish the molar absorptivities of the products are greater than those of the starting materials. The singlet oxygen quantum yield and the photodegradation of the products showed properties that are similar to bixin (11). Both the dimer (25) and the trimer (26) showed low fluorescence. The trimer (26) exhibited a high Stokes shift. In DMSO the compounds did not present aggregation, but in water the compounds proved to be hydrophobic. Further PDT applications will be performed in order to evaluate the use of these compounds as photosensitizers in PDT ou photodiagnosis. |
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Lopes, Thais de AssisOliveira, Kleber Thiago dehttp://lattes.cnpq.br/3759761373942891http://lattes.cnpq.br/93252161074495531cc6c663-f9aa-4041-a7ec-4c1b4e957a102019-09-06T18:25:49Z2019-09-06T18:25:49Z2019-05-06LOPES, Thais de Assis. Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas. 2019. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2019. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11789.https://repositorio.ufscar.br/handle/ufscar/11789In the chapter 1, studies on photocatalysed reactions were carried out by porphyrins and other photocatalysts aiming at the formation of radicals in amino aromatic systems for subsequent addition reaction. More specifically, double functionalization C-H reaction were studied by oxidative cyclization of N,N-dimethylaniline (16) with N-phenylmaleimide (17) to obtain tetrahydroquinolines, both by SET (single electron transfer) using meso-tetraphenylporphyrin (TPP) and Electron Donor-Acceptor (EDA) complex. For the evaluated reaction, the use of the photocatalyst TPP presented no influence on the formation of the product. Thus, experiments were additionally performed using N, N-dimethylaniline (16) and varying different electrophiles, however, it was not possible to observe the formation of the expected tetrahydroquinolines. Using the substrate fumaronitrile (65) gave a product of interest (2-(methyl(phenyl)amino)acetonitrile) (72), from a radical reaction of N,N-dimethylaniline (16) with fumaronitrile (65). Further, exploratory optimization experiments were performed, but unsuccesfully. Due to the appearance of related publications in the literature, it was decided to no longer insist on these studies. In the chapter 2 the synthesis and photophysical studies of hybrid molecules between curcumin (6) and bixin (11) were carried out aiming at the production of some new photosensitizing molecules for PDT applications. Curcumin is a compound well known by our research group with a well-established synthesis. Bixin (11) was extracted from the seeds of annatto by a modified methodology established in the literature. After obtaining these starting materials, the syntheses of chimeric photosensitizing molecules, the dimer (25) and the trimer (26) were studied. After the syntheses and characterizations of these compounds, studies of their photophysical properties were carried out, namely, studies of molar absorptivity, singlet oxygen quantum yield, photodegradation study, fluorescence quantum yield and aggregation. From these studies it was possible do stablish the molar absorptivities of the products are greater than those of the starting materials. The singlet oxygen quantum yield and the photodegradation of the products showed properties that are similar to bixin (11). Both the dimer (25) and the trimer (26) showed low fluorescence. The trimer (26) exhibited a high Stokes shift. In DMSO the compounds did not present aggregation, but in water the compounds proved to be hydrophobic. Further PDT applications will be performed in order to evaluate the use of these compounds as photosensitizers in PDT ou photodiagnosis.No capítulo 1 foram desenvolvidos estudos sobre reações fotocatalisadas por porfirinas e outros fotocatalisadores visando a formação de radicais em sistemas amino-aromáticos para posterior reação de adição à eletrófilos. Mais especificamente, foram estudadas algumas reações de dupla funcionalização C-H pela ciclização oxidativa da N,N-dimetilanilina (16) com a N-fenilmaleimida (17) para a obtenção de tetra-hidroquinolinas, tanto por SET (single electron transfer) utilizando a meso-tetrafenilporfirina (TPP) quanto por complexo EDA (Electron Donor−Acceptor). Para a reação avaliada, o uso do fotocatalisador não teve influência na formação do produto. Sendo assim, prosseguiu-se os experimentos utilizando a N,N-dimetilanilina (16) e variando diferentes eletrófilos, contudo, não foi possível observar a formação das tetra-hidroquinolinas esperadas. Ao se utilizar o substrato fumaronitrila (60) obteve-se um produto de interesse (2-(metil(phenil)amino)acetonitrila) (72), vindo de uma reação radicalar da N,N-dimetilanilina (16) com o fumaronitrila (65). Dessa forma, foram realizados experimentos exploratórios de otimização do mesmo, entretanto, não foram obtidos resultados satisfatórios. Com os surgimentos de publicações correlatas na literatura e diante dos muitos insucessos na nossa abordagem de escopo das transformações pretendidas, resolveu-se não mais insistir nestes estudos. No capítulo 2 as sínteses e estudos fotofísicos de moléculas híbridas entre a curcumina (6) e a bixina (11) foram realizados visando a produção de algumas novas moléculas fotossensibilizadoras para aplicações em PDT. A curcumina é um composto muito conhecido pelo nosso grupo de pesquisa e sua síntese muito bem estabelecida. A bixina (11) foi extraída a partir das sementes do urucum através de uma metodologia estabelecida na literatura, contudo, com algumas adaptações realizadas. Após a obtenção destes materiais de partida de origem natural, foram realizadas as sínteses de moléculas fotossensibilizadoras quiméricas, o dímero (25) e o trímero (26), sendo o dímero, a união de uma molécula de curcumina (6) com uma de bixina (11) e o trímero, a união de uma curcumina (6) com duas de bixinas (11). Após as sínteses e caracterizações destes compostos, foram realizados estudos de suas propriedades fotofísicas, sendo: estudos de absortividade molar, rendimento quântico de oxigênio singlete, estudo de fotodegradação, rendimento quântico de fluorescência e agregação. Com os estudos pôde-se perceber que as absortividades molares dos produtos são maiores do que dos materiais de partida. O rendimento quântico de oxigênio singlete e a fotodegradação os produtos apresentaram propriedades que se assemelham a bixina (11). Tanto o dímero (25) quanto o trímero (26) apresentaram uma baixa fluorescência. O trímero (26) exibiu um alto deslocamento de Stokes. Em DMSO os compostos não apresentaram agregação, porém em água os compostos demonstraram ser hidrofóbicos.Não recebi financiamentoporUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarFotoquímicaDupla funcionalização C-HTerapia fotodinâmicaHíbridos molecularesPhotochemistryCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAFotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicasPhotocatalysis and its applications in oxidative cyclization reactions and photonic therapyinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisOnline600ae02a3fa-cd1d-4c64-9580-4ad2f3715a6finfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALDissertação Thais de Assis Lopes_versão corrigida.pdfDissertação Thais de Assis Lopes_versão corrigida.pdfapplication/pdf5239575https://repositorio.ufscar.br/bitstream/ufscar/11789/3/Disserta%c3%a7%c3%a3o%20Thais%20de%20Assis%20Lopes_vers%c3%a3o%20corrigida.pdfa6b4e33a754773859b711fe1540a83d9MD53LICENSElicense.txtlicense.txttext/plain; charset=utf-81957https://repositorio.ufscar.br/bitstream/ufscar/11789/5/license.txtae0398b6f8b235e40ad82cba6c50031dMD55TEXTDissertação Thais de Assis Lopes_versão corrigida.pdf.txtDissertação Thais de Assis Lopes_versão corrigida.pdf.txtExtracted texttext/plain158477https://repositorio.ufscar.br/bitstream/ufscar/11789/6/Disserta%c3%a7%c3%a3o%20Thais%20de%20Assis%20Lopes_vers%c3%a3o%20corrigida.pdf.txt51428716501d9c10bcf56322c3d6a9e3MD56THUMBNAILDissertação Thais de Assis Lopes_versão corrigida.pdf.jpgDissertação Thais de Assis Lopes_versão corrigida.pdf.jpgIM Thumbnailimage/jpeg8312https://repositorio.ufscar.br/bitstream/ufscar/11789/7/Disserta%c3%a7%c3%a3o%20Thais%20de%20Assis%20Lopes_vers%c3%a3o%20corrigida.pdf.jpg3a0c53f5b786d77a8dd018a1024b8d65MD57ufscar/117892023-09-18 18:31:38.627oai:repositorio.ufscar.br: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Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:38Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
dc.title.alternative.eng.fl_str_mv |
Photocatalysis and its applications in oxidative cyclization reactions and photonic therapy |
title |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
spellingShingle |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas Lopes, Thais de Assis Fotoquímica Dupla funcionalização C-H Terapia fotodinâmica Híbridos moleculares Photochemistry CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
title_short |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
title_full |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
title_fullStr |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
title_full_unstemmed |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
title_sort |
Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas |
author |
Lopes, Thais de Assis |
author_facet |
Lopes, Thais de Assis |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/9325216107449553 |
dc.contributor.author.fl_str_mv |
Lopes, Thais de Assis |
dc.contributor.advisor1.fl_str_mv |
Oliveira, Kleber Thiago de |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3759761373942891 |
dc.contributor.authorID.fl_str_mv |
1cc6c663-f9aa-4041-a7ec-4c1b4e957a10 |
contributor_str_mv |
Oliveira, Kleber Thiago de |
dc.subject.por.fl_str_mv |
Fotoquímica Dupla funcionalização C-H Terapia fotodinâmica Híbridos moleculares |
topic |
Fotoquímica Dupla funcionalização C-H Terapia fotodinâmica Híbridos moleculares Photochemistry CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Photochemistry |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
description |
In the chapter 1, studies on photocatalysed reactions were carried out by porphyrins and other photocatalysts aiming at the formation of radicals in amino aromatic systems for subsequent addition reaction. More specifically, double functionalization C-H reaction were studied by oxidative cyclization of N,N-dimethylaniline (16) with N-phenylmaleimide (17) to obtain tetrahydroquinolines, both by SET (single electron transfer) using meso-tetraphenylporphyrin (TPP) and Electron Donor-Acceptor (EDA) complex. For the evaluated reaction, the use of the photocatalyst TPP presented no influence on the formation of the product. Thus, experiments were additionally performed using N, N-dimethylaniline (16) and varying different electrophiles, however, it was not possible to observe the formation of the expected tetrahydroquinolines. Using the substrate fumaronitrile (65) gave a product of interest (2-(methyl(phenyl)amino)acetonitrile) (72), from a radical reaction of N,N-dimethylaniline (16) with fumaronitrile (65). Further, exploratory optimization experiments were performed, but unsuccesfully. Due to the appearance of related publications in the literature, it was decided to no longer insist on these studies. In the chapter 2 the synthesis and photophysical studies of hybrid molecules between curcumin (6) and bixin (11) were carried out aiming at the production of some new photosensitizing molecules for PDT applications. Curcumin is a compound well known by our research group with a well-established synthesis. Bixin (11) was extracted from the seeds of annatto by a modified methodology established in the literature. After obtaining these starting materials, the syntheses of chimeric photosensitizing molecules, the dimer (25) and the trimer (26) were studied. After the syntheses and characterizations of these compounds, studies of their photophysical properties were carried out, namely, studies of molar absorptivity, singlet oxygen quantum yield, photodegradation study, fluorescence quantum yield and aggregation. From these studies it was possible do stablish the molar absorptivities of the products are greater than those of the starting materials. The singlet oxygen quantum yield and the photodegradation of the products showed properties that are similar to bixin (11). Both the dimer (25) and the trimer (26) showed low fluorescence. The trimer (26) exhibited a high Stokes shift. In DMSO the compounds did not present aggregation, but in water the compounds proved to be hydrophobic. Further PDT applications will be performed in order to evaluate the use of these compounds as photosensitizers in PDT ou photodiagnosis. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-09-06T18:25:49Z |
dc.date.available.fl_str_mv |
2019-09-06T18:25:49Z |
dc.date.issued.fl_str_mv |
2019-05-06 |
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.citation.fl_str_mv |
LOPES, Thais de Assis. Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas. 2019. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2019. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11789. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/11789 |
identifier_str_mv |
LOPES, Thais de Assis. Fotocatálise e suas aplicações em reações de ciclização oxidativa e terapia fotônicas. 2019. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2019. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11789. |
url |
https://repositorio.ufscar.br/handle/ufscar/11789 |
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por |
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por |
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600 |
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info:eu-repo/semantics/openAccess |
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openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química - PPGQ |
dc.publisher.initials.fl_str_mv |
UFSCar |
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Universidade Federal de São Carlos Câmpus São Carlos |
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Repositório Institucional da UFSCAR |
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