Mostrar el registro sencillo del ítem

dc.contributor.authorAlfonso Rodríguez, Ignacio
dc.contributor.authorBru Roig, Miriam
dc.contributor.authorBurguete, M. Isabel
dc.contributor.authorGarcia-Verdugo, Eduardo
dc.contributor.authorLuis, Santiago V.
dc.date.accessioned2012-11-08T15:04:11Z
dc.date.available2012-11-08T15:04:11Z
dc.date.issued2010
dc.identifier.citationChemistry - A European Journal (2010), 16, 4, p. 1246–1255ca_CA
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/10234/51439
dc.description.abstractThe self-assembling abilities of several pseudopeptidic macrocycles have been thoroughly studied both in the solid (SEM, TEM, FTIR) and in solution (NMR, UV, CD, FTIR) states. Detailed microscopy revealed large differences in the morphology of the self-assembling micro/nanostructures depending on the macrocyclic chemical structures. Self-assembly was triggered by the presence of additional methylene groups or by changing from para to meta geometry of the aromatic phenylene backbone moiety. More interestingly, the nature of the side chain also plays a fundamental role in some of the obtained nanostructures, thus producing structures from long fibers to hollow spheres. These nanostructures were obtained in different solvents and on different surfaces, thus implying that the chemical information for the self-assembly is contained in the molecular structure. Dilution NMR studies (chemical shift and self-diffusion rates) suggest the formation of incipient aggregates in solution by a combination of hydrogen-bonding and π–π interactions, thus implicating amide and aryl groups, respectively. Electronic spectroscopy further supports the π–π interactions because the compounds that lead to fibers show large hypochromic shifts in the UV spectra. Moreover, the fiber-forming macrocycles also showed a more intense CD signature. The hydrogen-bonding interactions within the nanostructures were also characterized by attenuated total-reflectance FTIR spectroscopy, which allowed us to monitor the complete transition from the solution to the dried nanostructure. Overall, we concluded that the self-assembly of this family of pseudopeptidic macrocycles is dictated by a synergic action of hydrogen-bonding and π–π interactions. The feasibility and geometrical disposition of these interactions finally render a hierarchical organization, which has been rationalized with a proposal of a model. The understanding of the process at the molecular level has allowed us to prepare hybrid soft materials.ca_CA
dc.format.extent10 p.ca_CA
dc.language.isoengca_CA
dc.publisherWiley-VCHca_CA
dc.rightsCopyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheimca_CA
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/*
dc.subjectmacrocyclesca_CA
dc.subjectnanostructuresca_CA
dc.subjectpseudopeptidesca_CA
dc.subjectself-assemblyca_CA
dc.subjectsupramolecular chemistryca_CA
dc.titleStructural diversity in the self-assembly of pseudopeptidic macrocyclesca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1002/chem.200902196
dc.rights.accessRightsinfo:eu-repo/semantics/closedAccessca_CA
dc.relation.publisherVersionhttp://onlinelibrary.wiley.com/doi/10.1002/chem.200902196/abstractca_CA
dc.type.versioninfo:eu-repo/semantics/publishedVersion


Ficheros en el ítem

FicherosTamañoFormatoVer

No hay ficheros asociados a este ítem.

Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem