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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/57925

    Título
    From Induced-Fit Assemblies to Ternary Inclusion Complexes with Fullerenes in Corannulene-Based Molecular Tweezers
    Autor
    Sacristán Martín, AdrianaAutoridad UVA
    Miguel San José, DanielAutoridad UVA Orcid
    Diez Varga, Alberto
    Barbero San Juan, HéctorAutoridad UVA Orcid
    Álvarez González, Celedonio ManuelAutoridad UVA Orcid
    Año del Documento
    2022
    Editorial
    American Chemical Society
    Descripción
    Producción Científica
    Documento Fuente
    Journal of Organic Chemistry, 2022, 87, 24, 16691–16706
    Résumé
    The participation of the tether moiety in fullerene recognition of corannulene-based molecular tweezers is known to be an important factor. In the present work, we describe the synthesis of a set of fullerene receptors bearing two corannulene units located at a suitable distance to effectively interact with C60 and C70. The tether comprises a fluorene-like scaffold where an assortment of different groups with variable electronic properties has been grafted. The photophysical and electrochemical properties of all final compounds have been unveiled and correlated to the donor/acceptor (DA) nature of the tether. Despite these strong variations, their affinity toward fullerenes cannot be correlated in any way to simple DA behavior as the main contribution to the interaction correspond to London dispersion forces. We found, however, that the sulfur-derived subfamily is able to adapt better to the fullerene outer surface slightly increasing the charge transfer and electrostatic attractive interactions being the most outstanding example the case of thiophene 4-S with C70 as it is capable of forming a ternary 2:1 inclusion complex in solution with an electronic binding energy that offsets entropy and desolvation penalties typically associated with higher-order inclusion complexes.
    Materias Unesco
    23 Química
    Palabras Clave
    Carbon nanomaterials
    Nanomateriales de carbono
    Mathematical methods
    Métodos matemáticos
    ISSN
    0022-3263
    Revisión por pares
    SI
    DOI
    10.1021/acs.joc.2c02345
    Patrocinador
    Ministerio de Ciencia, Innovación y Universidades (project (projects numbers PGC2018-096880-A-I00, MCIU/AEI/FEDER, UE, PGC2018-099470-B-I00, and MCIU/AEI/FEDER, UE)
    Version del Editor
    https://pubs.acs.org/doi/full/10.1021/acs.joc.2c02345
    Propietario de los Derechos
    © 2022 American Chemical Society
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/57925
    Tipo de versión
    info:eu-repo/semantics/publishedVersion
    Derechos
    openAccess
    Aparece en las colecciones
    • DEP63 - Artículos de revista [324]
    • CINQUIMA - Artículos de revista [162]
    • MIOMeT - Artículos de revista [51]
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    acs.joc.2c02345.pdf
    Tamaño:
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    Atribución 4.0 InternacionalExcepté là où spécifié autrement, la license de ce document est décrite en tant que Atribución 4.0 Internacional

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