Development of chemosensors for ions based on quinoxaline and quercetine derivatives

The development of artificial sensors for detecting ionic analytes in solution has attracted much attention, mainly to the biological and environmental areas, due to the possibility of rapid and high sensitivity analysis through simple and low-cost procedures. In the present work, syntheses of ne...

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Autor principal: Silva, Lilian Cavalcante da
Outros Autores: Menezes, Fabricio Gava
Formato: doctoralThesis
Idioma:pt_BR
Publicado em: Brasil
Assuntos:
Quimiossensores
Cátions
Ânions
Quinoxalina
Quercetina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Endereço do item:https://repositorio.ufrn.br/jspui/handle/123456789/28878
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id ri-123456789-28878
record_format dspace
institution Repositório Institucional
collection RI - UFRN
language pt_BR
topic Quimiossensores
Cátions
Ânions
Quinoxalina
Quercetina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
spellingShingle Quimiossensores
Cátions
Ânions
Quinoxalina
Quercetina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Silva, Lilian Cavalcante da
Development of chemosensors for ions based on quinoxaline and quercetine derivatives
description The development of artificial sensors for detecting ionic analytes in solution has attracted much attention, mainly to the biological and environmental areas, due to the possibility of rapid and high sensitivity analysis through simple and low-cost procedures. In the present work, syntheses of new quinoxaline derivatives were performed aiming to the detection of ions in aqueous solution. A total of nine derivatives compounds were obtained in good yields (65-84%) by a one-pot type procedure. The process begins with the oxidation of L-ascorbic acid, followed by reaction with two equivalents of o-phenylenediamine, to generate the AAQX compound which is converted to the final products via formation of a Schiff base from reaction with aromatic aldehydes. Nine compounds were synthesized and two were tested as chemosensors. It has been found that the final product obtained from benzaldehyde (N-(2-((Z)- benzylidene)amino)phenyl)-3-((1S,2S)-1,2,3-trihydroxypropyl)quinoxaline-2-carboxiamide) proved to be a selective chromogenic chemosensor for Cu2+ over the other cations in methanolwater solution 20%. The compound obtained from p-nitrobenzaldehyde (N-(2-((Z)-(4- nitrobenzylidene)amino)phenyl)-3-((1S,2S)-1,2,3-trihydroxypropyl)quinoxaline-2- carboxamide), was effective in detecting Fions in DMSO and DMSO-water solution (2.5%). The mechanism of action for these chemosensors has been proposed based on theoretical and spectroscopic data. Finally, a multidisciplinary proposal for chemistry lectures based on the capacity of a complex formed by Al3+ and quercetin natural product (QCT) for the detection of F - anions in an aqueous medium is presented. The proposal begins with the easy isolation of Rutin from the root of the Bredemeyera floribunda Willd plant, followed by a synthetic proposal for hydrolysis of the isolated substance, obtaining then quercetin. From quercetin was obtained a complex with Al3+ in a 2:1 stoichiometry (QCT: Al3+) that was characterized and applied as a chemosensor for Fby colorimetric, UV-visible and fluorescence tests. The multidisciplinary character of this project involves the areas of natural products, synthesis, complex chemistry, and theoretical calculations, and is, therefore, able to provide relevant stimuli for the chemistry student in their undergraduate courses.
author2 Menezes, Fabricio Gava
author_facet Menezes, Fabricio Gava
Silva, Lilian Cavalcante da
format doctoralThesis
author Silva, Lilian Cavalcante da
author_sort Silva, Lilian Cavalcante da
title Development of chemosensors for ions based on quinoxaline and quercetine derivatives
title_short Development of chemosensors for ions based on quinoxaline and quercetine derivatives
title_full Development of chemosensors for ions based on quinoxaline and quercetine derivatives
title_fullStr Development of chemosensors for ions based on quinoxaline and quercetine derivatives
title_full_unstemmed Development of chemosensors for ions based on quinoxaline and quercetine derivatives
title_sort development of chemosensors for ions based on quinoxaline and quercetine derivatives
publisher Brasil
publishDate 2020
url https://repositorio.ufrn.br/jspui/handle/123456789/28878
work_keys_str_mv AT silvaliliancavalcanteda developmentofchemosensorsforionsbasedonquinoxalineandquercetinederivatives
_version_ 1773966771909296128
spelling ri-123456789-288782020-05-10T07:30:09Z Development of chemosensors for ions based on quinoxaline and quercetine derivatives Silva, Lilian Cavalcante da Menezes, Fabricio Gava Freitas, Júlio Cézar de Oliveira Santos, Luciene da Silva Cristiano, Rodrigo Pinheiro, Sávio Moita Quimiossensores Cátions Ânions Quinoxalina Quercetina CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA The development of artificial sensors for detecting ionic analytes in solution has attracted much attention, mainly to the biological and environmental areas, due to the possibility of rapid and high sensitivity analysis through simple and low-cost procedures. In the present work, syntheses of new quinoxaline derivatives were performed aiming to the detection of ions in aqueous solution. A total of nine derivatives compounds were obtained in good yields (65-84%) by a one-pot type procedure. The process begins with the oxidation of L-ascorbic acid, followed by reaction with two equivalents of o-phenylenediamine, to generate the AAQX compound which is converted to the final products via formation of a Schiff base from reaction with aromatic aldehydes. Nine compounds were synthesized and two were tested as chemosensors. It has been found that the final product obtained from benzaldehyde (N-(2-((Z)- benzylidene)amino)phenyl)-3-((1S,2S)-1,2,3-trihydroxypropyl)quinoxaline-2-carboxiamide) proved to be a selective chromogenic chemosensor for Cu2+ over the other cations in methanolwater solution 20%. The compound obtained from p-nitrobenzaldehyde (N-(2-((Z)-(4- nitrobenzylidene)amino)phenyl)-3-((1S,2S)-1,2,3-trihydroxypropyl)quinoxaline-2- carboxamide), was effective in detecting Fions in DMSO and DMSO-water solution (2.5%). The mechanism of action for these chemosensors has been proposed based on theoretical and spectroscopic data. Finally, a multidisciplinary proposal for chemistry lectures based on the capacity of a complex formed by Al3+ and quercetin natural product (QCT) for the detection of F - anions in an aqueous medium is presented. The proposal begins with the easy isolation of Rutin from the root of the Bredemeyera floribunda Willd plant, followed by a synthetic proposal for hydrolysis of the isolated substance, obtaining then quercetin. From quercetin was obtained a complex with Al3+ in a 2:1 stoichiometry (QCT: Al3+) that was characterized and applied as a chemosensor for Fby colorimetric, UV-visible and fluorescence tests. The multidisciplinary character of this project involves the areas of natural products, synthesis, complex chemistry, and theoretical calculations, and is, therefore, able to provide relevant stimuli for the chemistry student in their undergraduate courses. O desenvolvimento de sensores artificiais para detecção de analitos iônicos em solução tem atraído grande atenção, principalmente, para as áreas biológica e ambiental, em função da possibilidade de análises rápidas e de alta sensibilidade, por meio de procedimentos simples e de baixo custo. No presente trabalho foram realizadas sínteses de novos derivados de quinoxalina com o objetivo de aplicá-los na detecção de íons em solução aquosa. Um total de nove compostos derivados foram obtidos com bons rendimentos (65-84%) por um procedimento do tipo one-pot. O processo tem início com a oxidação do ácido L-ascórbico, seguido da reação com dois equivalentes de o-fenilenodiamina para gerar o composto AAQX que é convertido nos produtos finais via formação de uma base de Schiff a partir da reação com aldeídos aromáticos. Entre os nove compostos sintetizados, dois foram testados como quimiossensores. Foi verificado que o produto final obtido a partir do benzaldeído (N-[(E)-2- (fenilmetilideno)amino)fenil]‐3‐(1,2,3‐trihidroxipropil)naftaleno‐2‐carboxamida) mostrou-se um quimiossensor cromogênico seletivo para o íon Cu2+ frente a outros cátions em solução de metanol-água 20%. O composto obtido a partir do p-nitrobenzaldeído (N-[(E)-2-(4- nitrobenzilideno)amino)fenil]-3-((1S,2S)-1,2,3-trihidroxipropil)quinoxalina-2-carboxamida), foi eficaz na detecção de íons Fem DMSO e em solução DMSO-água (2,5%). Os mecanismos de ação desses quimiossensores foram propostos com base em dados espectroscópicos e teóricos. Por fim, uma proposta multidisciplinar para aulas de Química com base na capacidade de um complexo formado por Al3+ e o produto natural quercetina (QCT) para detecção de ânions Fem meio aquoso é apresentada. A proposta se inicia com o fácil isolamento de Rutina a partir da raiz da planta Bredemeyera floribunda Willd, seguido de uma proposta sintética de hidrólise da substância isolada, obtendo-se a quercetina. A partir da quercetina obteve-se um complexo com Al3+ em uma estequiometria 2:1 (QCT:Al3+) que foi caracterizado e aplicado como quimiossensor para Fpor meio de testes colorimétricos, UV-visível e fluorescência. O caráter multidisciplinar desse projeto envolve as áreas de produtos naturais, síntese, Química dos complexos e cálculos teóricos, sendo, portanto, capaz de fornecer estímulos relevantes para o estudante de Química em seus cursos de formação. 2020-05-04T18:43:12Z 2020-05-04T18:43:12Z 2020-02-10 doctoralThesis SILVA, Lilian Cavalcante da. Development of chemosensors for ions based on quinoxaline and quercetine derivatives. 2020. 110f. Tese (Doutorado em Química) - Centro de Ciências Exatas e da Terra, Universidade Federal do Rio Grande do Norte, Natal, 2020. https://repositorio.ufrn.br/jspui/handle/123456789/28878 pt_BR Acesso Aberto application/pdf Brasil UFRN PROGRAMA DE PÓS-GRADUAÇÃO EM QUÍMICA

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