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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/65456

    Título
    Octapodal Corannulene Porphyrin-Based Assemblies: Allosteric Behavior in Fullerene Hosting
    Autor
    Ferrero, Sergio
    Barbero San Juan, HéctorAutoridad UVA Orcid
    Miguel San José, DanielAutoridad UVA Orcid
    García Rodríguez, RaúlAutoridad UVA Orcid
    Álvarez González, Celedonio ManuelAutoridad UVA Orcid
    Año del Documento
    2020
    Editorial
    American Chemical Society
    Descripción
    Producción Científica
    Documento Fuente
    The Journal of Organic Chemistry, marzo 2020, 85, 7, 4918–4926
    Abstract
    An octapodal corannulene-based supramolecular system has been prepared by introducing eight corannulene moieties in a porphyrin scaffold. Despite the potential of this double picket fence porphyrin for double-tweezer behavior, NMR titrations show exclusive formation of 1:1 adducts. The system exhibits very strong affinity for C60 and C70 (K1 = (2.71 ± 0.08) × 104 and (2.13 ± 0.1) × 105 M–1, respectively), presenting selectivity for the latter. Density functional theory (DFT) calculations indicate that, in addition to the four corannulene units, the relatively flexible porphyrin tether actively participates in the recognition process, resulting in a strong synergistic effect. This leads to a very strong interaction with C60, which in turn also induces a large structural change on the other face (second potential binding site), leading to a negative allosteric effect. We also introduced Zn2+ in the porphyrin core in an attempt to modulate its flexibility. The resulting metalloporphyrin also displayed single-tweezer behavior, albeit with slightly smaller binding constants for C60 and C70, suggesting that the effect of the coordination of fullerene to one face of our supramolecular platform was still transmitted to the other face, leading to the deactivation of the second potential binding site.
    Materias Unesco
    2304 Química Macromolecular
    Palabras Clave
    Carbon nanomaterials
    Molecular interactions
    Nanospheres
    Pyrroles
    Supramolecular chemistry
    ISSN
    0022-3263
    Revisión por pares
    SI
    DOI
    10.1021/acs.joc.0c00072
    Patrocinador
    Este trabajo forma parte de los proyectos de investigación MCIU/AEI/FEDER PGC2018-096880-A-I00, y PGC2018-099470-B-I00
    Version del Editor
    https://doi.org/10.1021/acs.joc.0c00072
    Propietario de los Derechos
    © 2020 American Chemical Society
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/65456
    Tipo de versión
    info:eu-repo/semantics/acceptedVersion
    Derechos
    openAccess
    Collections
    • MIOMeT - Artículos de revista [51]
    • CINQUIMA - Artículos de revista [162]
    • DEP63 - Artículos de revista [322]
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    Attribution-NonCommercial-NoDerivatives 4.0 InternacionalExcept where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivatives 4.0 Internacional

    Universidad de Valladolid

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