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Authors
Advisor(s)
Abstract(s)
Nesta dissertação são descritas as sínteses de novos polímeros conjugados do tipo fenileno-etinileno baseados em calix[4]arenos e em constituintes quirais de origem natural para aplicação à química sensorial.
A preparação destes polímeros envolveu a síntese e caracterização de monómeros precursores possuindo unidades de calixareno e unidades de glucose pentaacetato. Os polímeros sintetizados foram analisados por espectroscopia de infravermelho com transformada de Fourier, ressonância magnética nuclear de protão e cromatografia de permeação em gel. As propriedades fotofísicas e quirópticas destes materiais foram estudadas recorrendo a técnicas de absorção de estado fundamental, fluorescência de estado estacionário e dicroísmo circular.
Perspectivando a potencial aplicação destes poli(fenileno-etinilenos) como sensores fluorescentes, os materiais poliméricos sintetizados foram posteriormente testados na detecção de nitroaromáticos e nitroanilinas em solução e em filme. Para os vários analitos estudados é de destacar em ambos os materiais uma elevada sensibilidade e selectividade para ácido pícrico.
Adicionalmente, devido à natureza quiral dos polímeros conjugados preparados, foram realizados ensaios exploratórios de enantiodiscriminação utilizando metilbenzilaminas enantioméricas, recorrendo a técnicas de dicroísmo circular e absorção de estado fundamental.
Abstract: This dissertation describes the synthesis of new conjugated polymers of phenylene-ethynylene type based on calix[4]arenes and chiral constituents of natural origin for application to sensory chemistry. The preparation of these polymers required the synthesis and characterization of starting monomers possessing calixarene and glucose pentaacetate units. The synthesized polymers were analyzed by Fourier transform infrared, proton nuclear magnetic resonance and gel permeation chromatography. The photophysical and chiroptical properties of these materials were studied using the ground state absorption techniques, steady-state fluorescence and circular dichroism. Looking ahead to the potential application of thesepoly(phenylene-ethylene) as fluorescent sensors, the synthesized polymeric materials were studied and tested in the detection of nitroaromatic compounds and nitroanilines in solution and in film. Both polymers reveal high sensibility and selectivity for picric acid. Additionally, due to the chiral nature of the prepared conjugated polymers, exploratory tests of enantiodiscrimination of chiral methylbenzylamines were undertaken, using circular dichroism and ground state absorption techniques.
Abstract: This dissertation describes the synthesis of new conjugated polymers of phenylene-ethynylene type based on calix[4]arenes and chiral constituents of natural origin for application to sensory chemistry. The preparation of these polymers required the synthesis and characterization of starting monomers possessing calixarene and glucose pentaacetate units. The synthesized polymers were analyzed by Fourier transform infrared, proton nuclear magnetic resonance and gel permeation chromatography. The photophysical and chiroptical properties of these materials were studied using the ground state absorption techniques, steady-state fluorescence and circular dichroism. Looking ahead to the potential application of thesepoly(phenylene-ethylene) as fluorescent sensors, the synthesized polymeric materials were studied and tested in the detection of nitroaromatic compounds and nitroanilines in solution and in film. Both polymers reveal high sensibility and selectivity for picric acid. Additionally, due to the chiral nature of the prepared conjugated polymers, exploratory tests of enantiodiscrimination of chiral methylbenzylamines were undertaken, using circular dichroism and ground state absorption techniques.
Description
Trabalho Final de Mestrado para obtenção do grau de Mestre em Engenharia Química e Biológica
Keywords
Calixareno Calixarene Poli(fenileno-etinileno) Poly(phenylene-ethynylene) Quiralidade Chirality Glucose Sensor
Pedagogical Context
Citation
VELHO, Mariana Filipa Gaspar - Novos polímeros conjugados baseados em calixarenos contendo fontes quirais de origem natural: síntese, propriedades e aplicações sensoriais. Lisboa: Instituto Superior de Engenharia de Lisboa, 2015. Dissertação de mestrado.
Publisher
Instituto Superior de Engenharia de Lisboa