[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino
Ano de defesa: | 2021 |
---|---|
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/1/23274 |
Resumo: | Rotaxanes are widely studied for their ability to move one component relative to another. Intercomponent interactions are widely studied in solution and have been gaining more field in the crystalline solid state. Intermolecular interactions in rotaxanes are still a field to be explored. This emphasizes the importance of studying intercomponent and intermolecular interactions to understand the behavior of these molecules in the crystalline solid state. Therefore, this thesis uses rotaxanes as models to understand the formation of different crystalline phases and evaluate the influence of intercomponent and intermolecular interactions in the crystallization process. For a series of rotaxanes containing Leigh-type macrocycle, self-assembly, solvates, and the formation of different polymorphic phases were evaluated. A new series of [2]- and [3]rotaxanes with two stations was synthesized and evaluated regarding intercomponent and intermolecular interactions. The studied rotaxanes showed similar general stages of crystallization, in which in the first stage there is the formation of one-dimensional nuclei and, in less cases, dimers. A wide molecular complementarity was observed, with a high contact area and a large number of interaction paths in the formed nuclei, which prevent the occurrence of specific interactions capable of directing the formation of crystals. This behavior can be explained by the intrinsic molecular topology of rotaxane molecules. The participation of the solvent during crystallization was evaluated and showed that the solvent can be easily trapped between the one-dimensional and dimeric nuclei during the last stages of crystallization. In one example, it was observed that its topology favored the entrapment of water molecules between the rotaxanes that form the one-dimensional nucleus in the first crystallization stage, and not because of the nuclei approximation. Initial insights into the contribution of solvents to the stabilization energy of solvates have been provided. Different polymorphic forms, with the solvent and temperature conditions to obtain each phase, were reported. The key to understand the existence of polymorphs at room temperature lies in the first crystallization nuclei to be formed, as both have similar stabilization energies at this point. The two-station thread allowed to obtain molecules of [2]- and [3]rotaxanes as a function of small modification in the stoppers groups. New parameters and approaches at the intercomponent and intermolecular level, to guide the interpretation of self-assembly, solvates, and polymorphs of rotaxane molecules, have been provided. |
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2021-12-13T18:04:26Z2021-12-13T18:04:26Z2021-07-30http://repositorio.ufsm.br/handle/1/23274Rotaxanes are widely studied for their ability to move one component relative to another. Intercomponent interactions are widely studied in solution and have been gaining more field in the crystalline solid state. Intermolecular interactions in rotaxanes are still a field to be explored. This emphasizes the importance of studying intercomponent and intermolecular interactions to understand the behavior of these molecules in the crystalline solid state. Therefore, this thesis uses rotaxanes as models to understand the formation of different crystalline phases and evaluate the influence of intercomponent and intermolecular interactions in the crystallization process. For a series of rotaxanes containing Leigh-type macrocycle, self-assembly, solvates, and the formation of different polymorphic phases were evaluated. A new series of [2]- and [3]rotaxanes with two stations was synthesized and evaluated regarding intercomponent and intermolecular interactions. The studied rotaxanes showed similar general stages of crystallization, in which in the first stage there is the formation of one-dimensional nuclei and, in less cases, dimers. A wide molecular complementarity was observed, with a high contact area and a large number of interaction paths in the formed nuclei, which prevent the occurrence of specific interactions capable of directing the formation of crystals. This behavior can be explained by the intrinsic molecular topology of rotaxane molecules. The participation of the solvent during crystallization was evaluated and showed that the solvent can be easily trapped between the one-dimensional and dimeric nuclei during the last stages of crystallization. In one example, it was observed that its topology favored the entrapment of water molecules between the rotaxanes that form the one-dimensional nucleus in the first crystallization stage, and not because of the nuclei approximation. Initial insights into the contribution of solvents to the stabilization energy of solvates have been provided. Different polymorphic forms, with the solvent and temperature conditions to obtain each phase, were reported. The key to understand the existence of polymorphs at room temperature lies in the first crystallization nuclei to be formed, as both have similar stabilization energies at this point. The two-station thread allowed to obtain molecules of [2]- and [3]rotaxanes as a function of small modification in the stoppers groups. New parameters and approaches at the intercomponent and intermolecular level, to guide the interpretation of self-assembly, solvates, and polymorphs of rotaxane molecules, have been provided.Os rotaxanos são amplamente estudados devido sua capacidade de um componente mover-se em relação ao outro. As interações intercomponentes são amplamente estudadas em solução e vem ganhando mais campo no estado sólido cristalino. Já as interações intermoleculares em rotaxanos permanecem ainda como um campo a ser explorado. Com isso, ressalta-se a importância de estudar as interações intercomponentes e intermoleculares como forma de entender o comportamento destas moléculas no estado sólido cristalino. Sendo assim, esta tese utiliza rotaxanos como modelos para compreender a formação de diferentes fases cristalinas e avaliar a influência das interações intercomponentes e intermoleculares no processo de cristalização. Para uma série de rotaxanos, contendo macrociclo do tipo Leigh, foram avaliadas a autoassociação, a formação de solvatos, a formação de diferentes fases polimórficas. Uma nova série de [2]- e [3]rotaxanos com duas estações foi sintetizada e avaliada as interações intercomponentes e intermoleculares. Os rotaxanos estudados apresentaram estágios gerais de cristalização semelhantes, em que no primeiro estágio ocorre a formação de núcleos unidimensionais e, em menos casos, de dímeros. Foi observado uma grande complementaridade molecular, com alta área de contato e grande número de caminhos de interação nos núcleos formados, o que dificulta a ocorrência de interações específicas capazes de direcionar a formação de cristais. Este comportamento pode ser explicado pela topologia molecular intrínseca das moléculas de rotaxano. A participação do solvente na cristalização foi avaliada e mostrou que o solvente pode ser facilmente preso entre os núcleos unidimensionais e diméricos durante as últimas etapas de cristalização. Em um exemplo, foi observado que a topologia favoreceu o aprisionamento de moléculas de água entre as moléculas de rotaxanos que formam o núcleo unidimensional no primeiro estágio de cristalização e não por consequência da aproximação dos núcleos. Percepções iniciais da contribuição de solventes na estabilização energética de solvatos foram fornecidas. Diferentes formas polimórficas, juntamente com as condições de solvente e temperatura para obter cada fase, foram reportadas. A chave para entender a existência dos polimorfos à temperatura ambiente está no primeiro núcleo de cristalização a ser formado, já que ambos têm energias de estabilização semelhantes neste ponto. O modelo de eixo molecular de duas estações permitiu a obtenção de moléculas de [2]- e [3]rotaxanos em função de pequena modificação no grupo volumoso terminal. Novos parâmetros e abordagens no nível intercomponente e intermolecular, para guiar a interpretação da autoassociação e da formação de solvatos e polimorfos de moléculas de rotaxanos, foram fornecidos.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccessRotaxanosQuímica supramolecularInterações intercomponenteInterações intermolecularesEngenharia de cristaisRotaxanesSupramolecular chemistryIntercomponent interactionsIntermolecular interactionsCrystal engineeringCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino[2]- and [3]rotaxanes as models to assess the influence of intercomponent and intermolecular interactions in the crystalline solid stateinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Hoerner, ManfredoFrizzo, Clarissa PiccininRosa, Fernanda AndreiaCánovas, José BernáErben , Mauricio Federicohttp://lattes.cnpq.br/6896595996701518Orlando, Tainára100600000000600600600600600600c28419d9-6027-4f9c-acd2-76e8067a85d182d95942-e652-4454-9357-efc32938d051382cd478-ff6b-491e-a5b6-34e54f126498bf4338e5-e87c-4326-93b7-60f8f505f466d8662a5f-28f9-41c1-a6af-67b2581ef1d4cfef97d5-38e8-4120-be0b-d4d84d97d7723c1bacf1-81f7-41f7-8e71-1b3080504135reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2021_ORLANDO_TAINÁRA.pdfTES_PPGQUÍMICA_2021_ORLANDO_TAINÁRA.pdfTese de Doutoradoapplication/pdf26516107http://repositorio.ufsm.br/bitstream/1/23274/1/TES_PPGQU%c3%8dMICA_2021_ORLANDO_TAIN%c3%81RA.pdf3509ffa8dadf59b9c79cd1e471c4c19dMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
dc.title.alternative.eng.fl_str_mv |
[2]- and [3]rotaxanes as models to assess the influence of intercomponent and intermolecular interactions in the crystalline solid state |
title |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
spellingShingle |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino Orlando, Tainára Rotaxanos Química supramolecular Interações intercomponente Interações intermoleculares Engenharia de cristais Rotaxanes Supramolecular chemistry Intercomponent interactions Intermolecular interactions Crystal engineering CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
title_full |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
title_fullStr |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
title_full_unstemmed |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
title_sort |
[2]- e [3]rotaxanos como modelos para avaliar a influência das interações intercomponentes e intermoleculares no estado sólido cristalino |
author |
Orlando, Tainára |
author_facet |
Orlando, Tainára |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.advisor-co1.fl_str_mv |
Hoerner, Manfredo |
dc.contributor.referee1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee2.fl_str_mv |
Rosa, Fernanda Andreia |
dc.contributor.referee3.fl_str_mv |
Cánovas, José Berná |
dc.contributor.referee4.fl_str_mv |
Erben , Mauricio Federico |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6896595996701518 |
dc.contributor.author.fl_str_mv |
Orlando, Tainára |
contributor_str_mv |
Martins, Marcos Antonio Pinto Hoerner, Manfredo Frizzo, Clarissa Piccinin Rosa, Fernanda Andreia Cánovas, José Berná Erben , Mauricio Federico |
dc.subject.por.fl_str_mv |
Rotaxanos Química supramolecular Interações intercomponente Interações intermoleculares |
topic |
Rotaxanos Química supramolecular Interações intercomponente Interações intermoleculares Engenharia de cristais Rotaxanes Supramolecular chemistry Intercomponent interactions Intermolecular interactions Crystal engineering CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Engenharia de cristais Rotaxanes Supramolecular chemistry Intercomponent interactions Intermolecular interactions Crystal engineering |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Rotaxanes are widely studied for their ability to move one component relative to another. Intercomponent interactions are widely studied in solution and have been gaining more field in the crystalline solid state. Intermolecular interactions in rotaxanes are still a field to be explored. This emphasizes the importance of studying intercomponent and intermolecular interactions to understand the behavior of these molecules in the crystalline solid state. Therefore, this thesis uses rotaxanes as models to understand the formation of different crystalline phases and evaluate the influence of intercomponent and intermolecular interactions in the crystallization process. For a series of rotaxanes containing Leigh-type macrocycle, self-assembly, solvates, and the formation of different polymorphic phases were evaluated. A new series of [2]- and [3]rotaxanes with two stations was synthesized and evaluated regarding intercomponent and intermolecular interactions. The studied rotaxanes showed similar general stages of crystallization, in which in the first stage there is the formation of one-dimensional nuclei and, in less cases, dimers. A wide molecular complementarity was observed, with a high contact area and a large number of interaction paths in the formed nuclei, which prevent the occurrence of specific interactions capable of directing the formation of crystals. This behavior can be explained by the intrinsic molecular topology of rotaxane molecules. The participation of the solvent during crystallization was evaluated and showed that the solvent can be easily trapped between the one-dimensional and dimeric nuclei during the last stages of crystallization. In one example, it was observed that its topology favored the entrapment of water molecules between the rotaxanes that form the one-dimensional nucleus in the first crystallization stage, and not because of the nuclei approximation. Initial insights into the contribution of solvents to the stabilization energy of solvates have been provided. Different polymorphic forms, with the solvent and temperature conditions to obtain each phase, were reported. The key to understand the existence of polymorphs at room temperature lies in the first crystallization nuclei to be formed, as both have similar stabilization energies at this point. The two-station thread allowed to obtain molecules of [2]- and [3]rotaxanes as a function of small modification in the stoppers groups. New parameters and approaches at the intercomponent and intermolecular level, to guide the interpretation of self-assembly, solvates, and polymorphs of rotaxane molecules, have been provided. |
publishDate |
2021 |
dc.date.accessioned.fl_str_mv |
2021-12-13T18:04:26Z |
dc.date.available.fl_str_mv |
2021-12-13T18:04:26Z |
dc.date.issued.fl_str_mv |
2021-07-30 |
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/1/23274 |
url |
http://repositorio.ufsm.br/handle/1/23274 |
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 |
dc.relation.authority.fl_str_mv |
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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 |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
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