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Tânia Ereira Sintra Síntese De Líquidos Iónicos Mais Benignos Para Aplicações Específicas Synthesis of More Benign Ioni

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Tânia Ereira Sintra Síntese De Líquidos Iónicos Mais Benignos Para Aplicações Específicas Synthesis of More Benign Ioni Universidade de Aveiro Departamento de Química 2017 TÂNIA EREIRA SÍNTESE DE LÍQUIDOS IÓNICOS MAIS BENIGNOS SINTRA PARA APLICAÇÕES ESPECÍFICAS SYNTHESIS OF MORE BENIGN IONIC LIQUIDS FOR SPECIFIC APPLICATIONS Universidade de Aveiro Departamento de Química 2017 TÂNIA EREIRA SÍNTESE DE LÍQUIDOS IÓNICOS MAIS BENIGNOS SINTRA PARA APLICAÇÕES ESPECÍFICAS SYNTHESIS OF MORE BENIGN IONIC LIQUIDS FOR SPECIFIC APPLICATIONS Tese apresentada à Universidade de Aveiro para cumprimento dos requisitos necessários à obtenção do grau de Doutor em Química, realizada sob a orientação científica do Professor Doutor João Manuel da Costa e Araújo Pereira Coutinho, Professor Catedrático do Departamento de Química da Universidade de Aveiro, e co-orientação da Doutora Sónia Patrícia Marques Ventura, Investigadora Auxiliar no Instituto de Materiais de Aveiro (CICECO), do Departamento de Química da Universidade de Aveiro. Apoio financeiro através da Apoio financeiro do POCTI no âmbito O doutorando agradece o apoio FCT/MEC, no âmbito do projeto do III Quadro Comunitário de Apoio. financeiro da FCT no âmbito do III PTDC/ATP-EAM/5331/2014. Co-financiamento do POPH/FSE. Quadro Comunitário de Apoio (SFRH/BD/85871/2012). Dedico este trabalho ao nº 128 da Rua 21 de Maio, Antões. o júri presidente Prof. Doutor António Manuel Rosa Pereira Caetano professor catedrático da Universidade de Aveiro Prof. Doutor Carlos Alberto Mateus Afonso professor catedrático da Faculdade de Farmácia da Universidade de Lisboa Prof. Doutor Artur Manuel Soares da Silva professor catedrático da Universidade de Aveiro Prof. Doutora Emília Tojo Suárez professora associada da Universidade de Vigo, Espanha Doutora Cristina Silva Pereira investigadora principal do Instituto de Tecnologia Química e Biológica da Universidade Nova de Lisboa Doutora Sónia Patrícia Marques Ventura investigadora auxiliar da Universidade de Aveiro agradecimentos Era uma vez um reino vestido de cor-de-rosa… O rosa que carreguei com orgulho estes 4 anos resulta de múltiplas pinceladas de várias cores, provenientes do arco-íris multidisciplinar que é o Path. Obrigada por toda a generosidade, paciência e conhecimentos transmitidos. Vou levar sempre comigo esta palete de cores. Gostaria de agradecer em particular ao Professor João Coutinho e à Doutora Sónia Ventura por terem orientado os meus traços nesta grande “pintura científica”. Doctor Peter Schulz and Doctor Mikhail Gantman, “danke schön” for all your attention and for your help during my three months in Erlangen. Neste reino a vivência é produto de muito amor, cumplicidade e dedicação do paizinho João, da mamã Dalita e da nenuca Didi. Obrigada por estarem sempre comigo. Estando eu a falar de reinos, não poderia faltar um princeso, o meu André. Obrigada por estares ao meu lado na governação do reino. Por fim, mas não menos importante, temos os restantes habitantes do mesmo: os avozinhos, os Sintras e os amigos. Obrigada por rechearem os meus dias de sorrisos. A história continua… … que venham as próximas aventuras! palavras-chave Líquidos iónicos, ajustabilidade, síntese, antioxidantes, seletores quirais, hidrótopos, tensioactivos, magnéticos, anião per-fluoro-tert-butóxido, ecotoxicidade. resumo Nas últimas décadas, os líquidos iónicos (ILs) têm sido alvo de elevado interesse quer por parte da academia como a nível industrial. Isto deve-se em grande parte às suas propriedades únicas, assim como à possibilidade de, através de uma apropriada combinação dos seus iões, ser possível ajustar as suas propriedades para uma dada aplicação. Assim, os ILs têm vindo a ser considerados uma abordagem inovador para a “Química verde” e para a sustentabilidade. Contudo, a sua solubilidade em água faz com que estes possam facilmente chegar ao ecossistema aquático, podendo representar um perigo para este. O principal objetivo deste trabalho é estudar novos ILs, mais sustentáveis, assim como algumas das suas potenciais aplicações. Assim, foram investigados ILs como sendo antioxidantes, seletores quirais, hidrótopos, surfactantes, compostos magnéticos, assim como novos compostos hidrofóbicos. Para cada classe de ILs, foi estudada a sua síntese, caracterização físico-química e perfil de ecotoxicidade. Os novos ILs antioxidantes preparados neste trabalho foram avaliados quanto à sua solubilidade em água, estabilidade térmica, citotoxicidade e ecotoxicidade. Foram também estudados vários ILs quirais, quer baseados em aniões quirais (derivados de vários aminoácidos e do ácido tartárico), quer em catiões quirais (derivados da quinina, L-prolina e L-valina), no que respeita à sua estabilidade térmica, rotação ótica e ecotoxicidade. Além disso, foi avaliado o impacto de diferentes estruturas químicas dos ILs, assim como da sua concentração, na solubilidade de fármacos com reduzida solubilidade em água, a fim de analisar o seu comportamento enquanto hidrótopos cataniónicos. Entre as estruturas mais hidrofóbicas referidas neste trabalho estão vários ILs com natureza surfactante e um IL hidrofóbico baseado no anião per-fluoro-tert- butóxido. Relativamente aos ILs com carácter surfactante, foram preparados ILs pertencentes à família dos imidazólios, amónios quaternários e fosfónios, sendo posteriormente avaliados quanto à sua natureza de agregação, propriedades térmicas, ecotoxicidade, e à sua capacidade em promover disrupção celular. Por sua vez, o IL baseado no anião per-fluoro-tert-butóxido foi estudado relativamente às suas propriedades físicas, tais como a sua densidade, viscosidade e tensão superficial, assim como à sua toxicidade. Por fim, 24 ILs magnéticos foram preparados conjugando o catião colínio com - 2- 2- 3- diferentes aniões magnéticos ([FeCl4] , [MnCl4] , [CoCl4] and [GdCl6] ), sendo seguidamente avaliados quanto à sua ecotoxicidade. Visando o desenho racional de novos ILs, foi desenvolvido um modelo preditivo QSAR, onde foram utilizandos os dados de ecotoxicidade medidos neste trabalho. As previsões deste modelo relativamente à não toxicidade de um certo número de novos ILs foram testadas com êxito através da síntese destes compostos e posterior avaliação da sua ecotoxicidade utilizando o bioensaio Microtox. keywords Ionic liquids, designer solvents, synthesis, antioxidants, chiral selectors, hydrotropes, surface-active, magnetics, per-fluoro-tert-butoxide anion, ecotoxicity. abstract Due to their unique properties, ionic liquids (ILs) have attracted an increased scientific and industrial attention in the last decades. The possibility of tailoring their properties for a specific task by the adequate combination of their ions, makes these ionic compounds good candidates for a wide range of different applications. Actually, ILs have been described as an innovative approach to the “Green Chemistry” and sustainability principles. However, their solubility in water allows their easy access to the aquatic compartment, which makes them potentially hazardous compounds to aquatic organisms. The main goal of this work is to study new, more environmental friendly, IL structures and their main applications. ILs as antioxidants, chiral selectors, hydrotropes, surface-active compounds, with magnetic properties, as well as, new hydrophobic compounds are investigated. The synthesis, physico-chemical characterization and ecotoxicity profile were studied for the various classes of task specific ILs evaluated. New cholinium-based ILs with antioxidant nature were studied regarding their solubility in water, thermal stability, cytotoxicity, and ecotoxicity. Moreover, a large range of chiral ILs (CILs) based on several chiral anions (derived from chiral amino acids and tartaric acid) and chiral cations (based on quinine, L-proline and L-valine), was investigated and their thermal stability, optical rotation and ecotoxicity evaluated. Furthermore, the impact of different ILs structures and concentrations on the solubility of poorly water-soluble drugs was studied, and their role as catanionic hydrotropes investigated. Among the most hydrophobic structures reported in this work are several surface-active ILs and a hydrophobic IL based on the per-fluoro-tert-butoxide anion. The tensioactive ILs, belonging to the imidazolium, quaternary ammonium and phospholium families were tested in terms of their aggregation behavior, thermal properties, ecotoxicity, and their capacity to promore cell disruption. On the other hand, the per-fluoro-tert-butoxide-based IL was evaluated regarding its physical properties, such as density, viscosity, and surface tension and toxicity. Finally, 24 magnetic ILs belonging to the cholinium - 2- 2- 3- family and using [FeCl4] , [MnCl4] , [CoCl4] and [GdCl6] as anions were investigated and their ecotoxicity evaluated. Aiming at the rational design of ILs, a predictive QSAR model was developed with our help, and using ecotoxicity data measured in this work. The predictions of this model concerning the non-toxicity of a number of novel ILs were successfully tested by synthesizing these compounds and evaluating their toxicity using the Microtox bioassay. Synthesis Of More Benign Ionic Liquids For Specific Applications -Contents- Contents List of Figures ..................................................................................................................................ii List of Schemes ................................................................................................................................ v List of Tables ................................................................................................................................... vi
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