Meglumine-based supramolecular amphiphiles: The effect of chain length

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.contributorLaboratory of Biopolymers and Biomaterials (BIOPOLMAT)-
Autor(es): dc.creatorAlonso, J. D.-
Autor(es): dc.creatorFerreira, L. M.B.-
Autor(es): dc.creatorOyafuso, M. H.-
Autor(es): dc.creatorCassimiro, D. L.-
Autor(es): dc.creatorBarud, H.-
Autor(es): dc.creatorRibeiro, C. A.-
Data de aceite: dc.date.accessioned2025-08-21T15:11:09Z-
Data de disponibilização: dc.date.available2025-08-21T15:11:09Z-
Data de envio: dc.date.issued2022-04-28-
Data de envio: dc.date.issued2022-04-28-
Data de envio: dc.date.issued2022-04-01-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.molliq.2022.118684-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/223415-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/223415-
Descrição: dc.descriptionSurfactants are amphiphilic substances that lower the surface tension or influence the surfaces' contact between two liquids. They are suitable for a wide range of industrial applications, often being used as emulsifiers. However, most of them are petroleum derivatives and generally are non-biodegradable. New synthetic surfactants have been reported in the literature using a covalent synthesis method, but it takes several steps and uses a large amount of toxic organic solvents. To overcome those drawbacks, we proposed a supramolecular green synthesis route. The acid-base reaction between meglumine (MEG) and two saturated carboxylic acids differing in chain size, undecanoate acid (UM, 11 carbons) and palmitic acid (PM, 16 carbons), were performed in a minimum quantity of organic solvent. The supra-amphiphiles, PM and UM, were analyzed by Nuclear Magnetic Resonance (NMR), Differential Scanning Calorimetry (DSC), Capillarity Viscosity, Small-angle X-ray scattering (SAXS), and Polarized Optical Microscopy (POM) in the presence and/or absence of water. We observed two distinct self-assembly behaviors in water. UM act as a surfactant since SAXS showed micellar aggregation, and its relative viscosity curve has no alteration. Additionally, the events present in DSC curves show no evidence of gel-sol transition due absence of stable hydrogen bonds. On the other hand, PM act as a supramolecular polymer, as evidenced by a baseline shift of the DSC curves due to the disruption of hydrogen bonds. Moreover, PM self-assembles in water in a liquid-crystalline arrangement with increasing viscosity in a concentration-dependent manner. SAXS studies showed the formation of lamellar and hexagonal mesophases. Based on these results, we proposed a model in which the adducts' supramolecular organization is dependent on the hydrophilic/hydrophobic balance. When it tends to the hydrophobic side, there is the formation of the supramolecular polymer. The Van der Waals interactions are necessary to organize the liquid-crystalline mesophase. Also, they are necessary to stabilize the hydrogen bonds between MEG/water, enabling the gel-sol transition, leading to new properties, like thermal reversibility observed in PM.-
Descrição: dc.descriptionChemistry Institute São Paulo State University, R. Prof. Francisco Degni, s/n, SP-
Descrição: dc.descriptionSchool of Pharmaceutical Sciences São Paulo State University, Rodovia Araraquara-Jau Km 1, SP-
Descrição: dc.descriptionUniversity of Araraquara (Uniara) Laboratory of Biopolymers and Biomaterials (BIOPOLMAT)-
Descrição: dc.descriptionChemistry Institute São Paulo State University, R. Prof. Francisco Degni, s/n, SP-
Descrição: dc.descriptionSchool of Pharmaceutical Sciences São Paulo State University, Rodovia Araraquara-Jau Km 1, SP-
Idioma: dc.languageen-
Relação: dc.relationJournal of Molecular Liquids-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectSupra-amphiphiles-
Palavras-chave: dc.subjectSupramolecular chemistry-
Palavras-chave: dc.subjectSupramolecular polymers-
Palavras-chave: dc.subjectSurfactants-
Título: dc.titleMeglumine-based supramolecular amphiphiles: The effect of chain length-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

Não existem arquivos associados a este item.