Understanding the affinity of bis-exTTF macrocyclic receptors towards fullerene recognition
| Autor: | Nazario Martín, Joaquín Calbo, Emilio M. Pérez, Juan Aragó, Enrique Ortí, Julia Villalva, Alberto de Juan |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Fullerene General Physics and Astronomy 02 engineering and technology Synergistic combination 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 3. Good health 0104 chemical sciences Alkyl ether chemistry.chemical_compound Crystallography chemistry Chlorobenzene Non-covalent interactions Physical and Theoretical Chemistry 0210 nano-technology Receptor |
| Zdroj: | Repositorio Institucional del Instituto Madrileño de Estudios Avanzados en Nanociencia instname |
| ISSN: | 1463-9084 1463-9076 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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