期刊
CHEMICAL SCIENCE
卷 4, 期 4, 页码 1462-1469出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc22250k
关键词
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资金
- Non-Equilibrium Energy Research Centre (NERC)
- U.S. Department of Energy, Office of Basic Sciences (DOE-BES) [DE-SC0000989, DE-SC0001059]
- National Science Foundation
- U.S. National Science Foundation [CHE-1012378]
- Argonne-Northwestern Solar Energy Research (ANSER) Center
Molecular reorganization around the core of C-60 has been achieved by electron transfer centered on pi-dimerizable viologen subunits located in a restricted region of space. Fullerene C-60 hexaadducts, featuring 12 viologen subunits, have been prepared by using copper-mediated Huisgen 1,3-dipolar cycloaddition of azides with alkynes. Detailed electrochemical studies, supported by UV-Vis and EPR spectroscopic analyses, demonstrate that the linkers bearing the viologen subunits attached to specific positions around the all-carbon sphere, allow the formation of six intramolecular pi-dimers. Theoretical calculations reveal that the close proximity of the orbitals of the viologen subunits attached to the C-60 facilitate the pi-dimerization of the bis-radical species. These investigations support the fact that the motion of discrete peripheral groups oriented around the all-carbon sphere of C-60 can be controlled electrochemically using noncovalent reversible interactions.
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