RT info:eu-repo/semantics/article
T1 From Induced-Fit Assemblies to Ternary Inclusion Complexes with Fullerenes in Corannulene-Based Molecular Tweezers
A1 Sacristán Martín, Adriana
A1 Miguel San José, Daniel
A1 Diez Varga, Alberto
A1 Barbero San Juan, Héctor
A1 Álvarez González, Celedonio Manuel
K1 Carbon nanomaterials
K1 Nanomateriales de carbono
K1 Mathematical methods
K1 Métodos matemáticos
K1 23 Química
AB 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.
PB American Chemical Society
SN 0022-3263
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/57925
UL https://uvadoc.uva.es/handle/10324/57925
LA eng
NO Journal of Organic Chemistry, 2022, 87, 24, 16691–16706
NO Producción Científica
DS UVaDOC
RD 24-nov-2024