Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 43, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202212279
Keywords
Anion-pi Interactions; Electrostatic Interactions; Hammet Analysis; London Dispersion Force; pi-pi Interactions
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Funding
- Asahi Glass Foundation
- JSPS KAKENHI [JP20K05472]
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In this study, a fullerene-based torsion balance was used as a model system to quantify noncovalent interactions between arenes and the fullerene surface. The folding equilibrium was analyzed to measure the contributions of different factors to the interactions.
Face-to-face noncovalent arene-fullerene interactions are important in several research fields such as synthetic chemistry, materials chemistry, and medicinal chemistry; however, their nature and strength are still poorly understood. In this study, we prepare a fullerene-based torsion balance containing thioanisole, phenol, naphthalene, azulene, and pyrene moieties as a unimolecular model system. Moreover, we compare the folding free energies between the folded and the unfolded conformers of a series of the molecular torsion balances to quantify noncovalent interactions between arenes and the fullerene surface. This work demonstrates that the contributions of polarizabilities, anionic charges, electronic dipole moments, and the number of arene rings to the interactions can be experimentally measured by analyzing the folding equilibrium of the molecular torsion balances.
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