Understanding the affinity of bis-exTTF macrocyclic receptors towards fullerene recognition

Literature Information

Publication Date 2019-05-20
DOI 10.1039/C9CP01735F
Impact Factor 3.676
Authors

Joaquín Calbo, Alberto de Juan, Juan Aragó, Julia Villalva, Emilio M. Pérez, Enrique Ortí


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Abstract

A new series of fullerene receptors based on exTTF macrocycles with alkyl ether chains of increasing length is reported. The novel macrocyclic receptors are able to favourably interact with fullerene C60 through a synergistic combination of π–π, CH⋯π and n⋯π noncovalent interactions. We identify that the highest affinity towards C60 recognition is achieved for the host with the tightest fit; that is, the smallest receptor with a cavity large enough to host the buckyball inside (log Ka = 5.2 in chlorobenzene at 298 K). However, besides this expected observation, theoretical calculations evidence that the most stable self-assembling configuration corresponds for all the receptors to an outside-ring binding mode, in which the C60 guest is out of the cavity of the receptor. The higher stability of this configuration results from the smaller deformation energy it implies for the receptor, and allows to explain the experimental trends in the association constants.

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Inside front cover

Cover

DOI: 10.1039/D0PY90161J

Back cover

2021-01-20 Cover

DOI: 10.1039/D1PY90008K

Front cover

Cover

DOI: 10.1039/D0PY90160A

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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