Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina
Ano de defesa: | 2020 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
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/1/23448 |
Resumo: | In this work, two classes of porphyrins were prepared, the first involving the synthesis of new calcogenoporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin, characterization and study of photophysical properties, and the second, the synthesis of new metalloporphyrins from previous thioaryl porphyrins, characterization and study of photophysical properties. For the first class of compounds, a synthetic route that synthesizes the synthesis of four compounds derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin is specialized. Tetrasubstituted calcogenporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin were used using p-methyl-diphenyl-diselenide, p-chloro-diphenyl-diselenide, diphenyl-diselenide and diphenyl-disulfide as a source of anion of arylcalcogen. Thus, the synthesis of calcogenoporphyrins occurred through a second order nucleophilic substitution reaction between 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin and a nucleophile derived from aryl-dicalcogen. The formation of the products depends on the control of the reaction time, and the amount of sodium borohydride. Thus a series of 4 new molecules of chalcogenpyrphyrins were displaced. In the synthetic route applied, the formation of products in good settings (58-65%) stands out, in a short reaction time, without the use of base in the reaction medium and with the use of reagents that are easy to handle. The compounds were characterized by ¹H and 77Se nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS-ESI (+)), electronic spectroscopy in the ultraviolet-visible (UV-vis) regions and fluorescent emission spectroscopy. In addition, quantum conformation studies of fluorescence and singlet oxygen generation (ΦΔ) were carried out. In addition, a second class of porphyrins was prepared, in all a series of 16 metalloporphyrins derived from zinc, copper, nickel and cobalt were synthesized from thioaryl porphyrins previously prepared. Through methodologies already outdated in the literature and with specific optimizations, all 16 metalloporphyrins were shipped with more than 95% yield. These new compounds were characterized by ¹H NMR and UV-Vis absorption and fluorescence emission spectroscopies. Metalloporphyrins with zinc present much higher values of quantum fluorescence supplements, when compared to the TPP standard, being up to 3 times higher for two examples. For the other metalloporphyrins, although presented fluorescence emission, the good quantum ones were much lower than the TPP standard. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2022-01-04T16:53:33Z2022-01-04T16:53:33Z2020-09-30http://repositorio.ufsm.br/handle/1/23448In this work, two classes of porphyrins were prepared, the first involving the synthesis of new calcogenoporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin, characterization and study of photophysical properties, and the second, the synthesis of new metalloporphyrins from previous thioaryl porphyrins, characterization and study of photophysical properties. For the first class of compounds, a synthetic route that synthesizes the synthesis of four compounds derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin is specialized. Tetrasubstituted calcogenporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin were used using p-methyl-diphenyl-diselenide, p-chloro-diphenyl-diselenide, diphenyl-diselenide and diphenyl-disulfide as a source of anion of arylcalcogen. Thus, the synthesis of calcogenoporphyrins occurred through a second order nucleophilic substitution reaction between 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin and a nucleophile derived from aryl-dicalcogen. The formation of the products depends on the control of the reaction time, and the amount of sodium borohydride. Thus a series of 4 new molecules of chalcogenpyrphyrins were displaced. In the synthetic route applied, the formation of products in good settings (58-65%) stands out, in a short reaction time, without the use of base in the reaction medium and with the use of reagents that are easy to handle. The compounds were characterized by ¹H and 77Se nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS-ESI (+)), electronic spectroscopy in the ultraviolet-visible (UV-vis) regions and fluorescent emission spectroscopy. In addition, quantum conformation studies of fluorescence and singlet oxygen generation (ΦΔ) were carried out. In addition, a second class of porphyrins was prepared, in all a series of 16 metalloporphyrins derived from zinc, copper, nickel and cobalt were synthesized from thioaryl porphyrins previously prepared. Through methodologies already outdated in the literature and with specific optimizations, all 16 metalloporphyrins were shipped with more than 95% yield. These new compounds were characterized by ¹H NMR and UV-Vis absorption and fluorescence emission spectroscopies. Metalloporphyrins with zinc present much higher values of quantum fluorescence supplements, when compared to the TPP standard, being up to 3 times higher for two examples. For the other metalloporphyrins, although presented fluorescence emission, the good quantum ones were much lower than the TPP standard.Neste trabalho foi realizada a preparação de duas classes de porfirinas, sendo a primeira envolvendo a síntese de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis(4-bromometilfenil)porfirina, caracterização e estudo das propriedades fotofísicas, e a segunda, a síntese de novas metaloporfirinas a partir de tioaril porfirinas anteriormente descritas, caracterização e estudo das propriedades fotofísicas. Para a primeira classe de compostos, desenvolveu-se uma rota sintética que permitiu a síntese de quatro compostos derivados da 5,10,15,20–tetrakis(4-bromometilfenil)porfirina. Foram obtidas calcogenoporfirinas tetrasubstituídas derivadas da 5,10,15,20–tetrakis(4-bromometilfenil)porfirina empregando p-metil-difenil-disseleneto, p-cloro-difenil-disseleneto, difenil-disseleneto e difenil-dissulfeto como fonte de ânion de arilcalcogênio. Desta forma, a síntese das calcogenoporfirinas ocorreu através de uma reação de substituição nucleofílica de segunda ordem entre a 5,10,15,20–tetrakis(4-bromometilfenil)porfirina e um nucleófilo derivado de aril-dicalcogeneto. A formação dos produtos dependeu do controle do tempo reacional, e da quantidade de borohidreto de sódio. Assim uma série de 4 moléculas inéditas de calcogênopirfirinas foram obtidas. Na rota sintética aplicada, destaca-se a formação dos produtos em bons rendimentos (58-65%), em curto tempo de reação, sem a utilização de base no meio reacional e com emprego de reagentes de fácil manuseio. Os compostos foram caracterizados por ressonância magnética nuclear (RMN) de ¹H e 77Se, espectrometria de massas de alta resolução (HRMS-ESI(+)), espectroscopia eletrônica nas regiões do ultravioleta-visível (UV-vis) e espectroscopia de emissão fluorescente. Ainda, foram elaborados estudos de rendimentos quânticos de fluorescência e geração de oxigênio singleto (ΦΔ). Adicionalmente, uma segunda classe de porfirinas foram preparadas, ao todo uma serie de 16 metaloporfirinas derivadas de zinco, cobre, níquel e cobalto foram sintetizadas a partir de tioaril porfirinas anteriormente preparadas. Através de metodologias já descritas na literatura e com otimizações pontuais, todas as 16 metaloporfirínas foram obtidas com mais de 95% de rendimento. Esses novos compostos foram caracterizados por RMN de ¹H e por espectroscopias de absorção UV-Vis e emissão de fluorescência. As metaloporfirinas com zinco apresentam valores bem superiores de rendimentos quânticos de fluorescência, se comparado ao padrão TPP, sendo até 3 vezes maiores para dois exemplos. Já para as demais metaloporfirínas, embora tenham apresentado emissão de fluorescência, os rendimentos quânticos foram bem inferiores ao padrão TPP.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade 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/openAccessPropriedades fotofísicasSelenoporfirinasTioporfirinasPhotophysical propertiesSelenoporphyrinsThioporphyrinsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirinaSynthesis, characterization, photophysical study of new chalcogenporphyrins derived from 5,10,15,20-tetrakis(4-bromometilfenil)porphyrininfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Dalcol, Ionara IrionMorel, Aldemir FariasSouza, Diego deMostardeiro, Marco Auréliohttp://lattes.cnpq.br/6515346350624787Garcia, Fábio Dutra10060000000060060060060060060060009fef019-ac43-4d8b-83d3-3565e4686d7b98d3a25d-c852-4a5a-b35e-4da08a2103d62cbacb00-be94-498b-9c77-1d47963baf690536d1fb-e2cd-41ad-b277-9f916a1a037160da2236-e29c-4d57-a253-bc830d7534fcbdd40376-c7b0-4451-8b43-4ebfeada90fcreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMO autor da tese, Fabio Dutra Garcia, informou presencialmente na Biblioteca Central que o examinador Josimar Vargas, cujo nome constou na Ata de defesa, foi substituído pelo suplente Aldemir Farias Morel, o qual assinou a folha de aprovação.ORIGINALTES_PPGQUÍMICA_2020_GARCIA_FÁBIO.pdfTES_PPGQUÍMICA_2020_GARCIA_FÁBIO.pdfTese de doutoradoapplication/pdf4712971http://repositorio.ufsm.br/bitstream/1/23448/1/TES_PPGQU%c3%8dMICA_2020_GARCIA_F%c3%81BIO.pdf464ed4aba454f6557948fe611063a504MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
dc.title.alternative.eng.fl_str_mv |
Synthesis, characterization, photophysical study of new chalcogenporphyrins derived from 5,10,15,20-tetrakis(4-bromometilfenil)porphyrin |
title |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
spellingShingle |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina Garcia, Fábio Dutra Propriedades fotofísicas Selenoporfirinas Tioporfirinas Photophysical properties Selenoporphyrins Thioporphyrins CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
title_full |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
title_fullStr |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
title_full_unstemmed |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
title_sort |
Síntese, caracterização e estudo fotofísico de novas calcogenoporfirinas derivadas da 5,10,15,20–tetrakis (4-bromometilfenil)porfirina |
author |
Garcia, Fábio Dutra |
author_facet |
Garcia, Fábio Dutra |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee1.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee2.fl_str_mv |
Morel, Aldemir Farias |
dc.contributor.referee3.fl_str_mv |
Souza, Diego de |
dc.contributor.referee4.fl_str_mv |
Mostardeiro, Marco Aurélio |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6515346350624787 |
dc.contributor.author.fl_str_mv |
Garcia, Fábio Dutra |
contributor_str_mv |
Rodrigues, Oscar Endrigo Dorneles Dalcol, Ionara Irion Morel, Aldemir Farias Souza, Diego de Mostardeiro, Marco Aurélio |
dc.subject.por.fl_str_mv |
Propriedades fotofísicas Selenoporfirinas Tioporfirinas |
topic |
Propriedades fotofísicas Selenoporfirinas Tioporfirinas Photophysical properties Selenoporphyrins Thioporphyrins CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Photophysical properties Selenoporphyrins Thioporphyrins |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, two classes of porphyrins were prepared, the first involving the synthesis of new calcogenoporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin, characterization and study of photophysical properties, and the second, the synthesis of new metalloporphyrins from previous thioaryl porphyrins, characterization and study of photophysical properties. For the first class of compounds, a synthetic route that synthesizes the synthesis of four compounds derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin is specialized. Tetrasubstituted calcogenporphyrins derived from 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin were used using p-methyl-diphenyl-diselenide, p-chloro-diphenyl-diselenide, diphenyl-diselenide and diphenyl-disulfide as a source of anion of arylcalcogen. Thus, the synthesis of calcogenoporphyrins occurred through a second order nucleophilic substitution reaction between 5,10,15,20 - tetrakis (4-bromomethylphenyl) porphyrin and a nucleophile derived from aryl-dicalcogen. The formation of the products depends on the control of the reaction time, and the amount of sodium borohydride. Thus a series of 4 new molecules of chalcogenpyrphyrins were displaced. In the synthetic route applied, the formation of products in good settings (58-65%) stands out, in a short reaction time, without the use of base in the reaction medium and with the use of reagents that are easy to handle. The compounds were characterized by ¹H and 77Se nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS-ESI (+)), electronic spectroscopy in the ultraviolet-visible (UV-vis) regions and fluorescent emission spectroscopy. In addition, quantum conformation studies of fluorescence and singlet oxygen generation (ΦΔ) were carried out. In addition, a second class of porphyrins was prepared, in all a series of 16 metalloporphyrins derived from zinc, copper, nickel and cobalt were synthesized from thioaryl porphyrins previously prepared. Through methodologies already outdated in the literature and with specific optimizations, all 16 metalloporphyrins were shipped with more than 95% yield. These new compounds were characterized by ¹H NMR and UV-Vis absorption and fluorescence emission spectroscopies. Metalloporphyrins with zinc present much higher values of quantum fluorescence supplements, when compared to the TPP standard, being up to 3 times higher for two examples. For the other metalloporphyrins, although presented fluorescence emission, the good quantum ones were much lower than the TPP standard. |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-09-30 |
dc.date.accessioned.fl_str_mv |
2022-01-04T16:53:33Z |
dc.date.available.fl_str_mv |
2022-01-04T16:53:33Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/23448 |
url |
http://repositorio.ufsm.br/handle/1/23448 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 |
dc.relation.authority.fl_str_mv |
09fef019-ac43-4d8b-83d3-3565e4686d7b 98d3a25d-c852-4a5a-b35e-4da08a2103d6 2cbacb00-be94-498b-9c77-1d47963baf69 0536d1fb-e2cd-41ad-b277-9f916a1a0371 60da2236-e29c-4d57-a253-bc830d7534fc bdd40376-c7b0-4451-8b43-4ebfeada90fc |
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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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
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UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
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atendimento.sib@ufsm.br||tedebc@gmail.com |
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