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Título
From Induced-Fit Assemblies to Ternary Inclusion Complexes with Fullerenes in Corannulene-Based Molecular Tweezers
Autor
Año del Documento
2022
Editorial
American Chemical Society
Descripción
Producción Científica
Documento Fuente
Journal of Organic Chemistry, 2022, 87, 24, 16691–16706
Abstract
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
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
Propietario de los Derechos
© 2022 American Chemical Society
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
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