Synthesis and Conformational Analysis of Fullerene Torsion Balances for Assessing the Contribution of Dispersion and Anionic Character in Non‐Covalent Arene–Fullerene Interactions
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Published:2023-06-16
Issue:44
Volume:29
Page:
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ISSN:0947-6539
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Container-title:Chemistry – A European Journal
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language:en
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Short-container-title:Chemistry A European J
Author:
Yamada Michio1ORCID,
Sahara Koki1,
Koizumi Masaaki1,
Maeda Yutaka1ORCID,
Suzuki Mitsuaki2ORCID
Affiliation:
1. Department of Chemistry Tokyo Gakugei University Nukuikitamachi 4-1-1 Koganei Tokyo 184-8501 Japan
2. Department of Chemistry Josai University Sakado Saitama 350-0295 Japan
Abstract
AbstractWe employ a molecular torsion balance displaying bifurcated conformational isomerism to quantitatively evaluate the non‐covalent interactions between the fullerene surface and substituted arene moieties containing elements with high atomic numbers, as well as the thermodynamic processes involved in the folding equilibrium using nuclear magnetic resonance spectroscopy. The interaction between fullerene and haloaryl groups was stronger in cases where the introduced halogen had a higher atomic number, indicating that dispersion forces play a significant role in the interaction between fullerenes and 4‐haloaryl groups. The dispersion term also significantly contributed to the interaction between fullerene and the 4‐mercaptophenyl group. Moreover, the addition of an appropriate base to the 4‐mercaptophenyl‐appended torsion balance formed the corresponding thiophenolate anion, resulting in a large negative change in the folding free energy in CDCl3. Detailed analysis suggested that the observed attractive anionic arene–fullerene interactions predominantly originated from solvation effects.
Funder
Asahi Glass Foundation
Japan Society for the Promotion of Science
Shorai Foundation for Science and Technology
Subject
General Chemistry,Catalysis,Organic Chemistry
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