π-Dimerization of viologen subunits around the core of C60from twelve to six directions

Julien Iehl, Marco Frasconi, Henri Pierre Jacquot De Rouville, Nicolas Renaud, Scott M. Dyar, Nathan L. Strutt, Ranaan Carmieli, Michael R. Wasielewski, Mark A. Ratner, Jean François Nierengarten, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

Molecular reorganization around the core of C60has been achieved by electron transfer centered on π-dimerizable viologen subunits located in a restricted region of space. Fullerene C60hexaadducts, 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 π-dimers. Theoretical calculations reveal that the close proximity of the orbitals of the viologen subunits attached to the C60facilitate the π-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 C60can be controlled electrochemically using noncovalent reversible interactions.

Original languageEnglish (US)
Pages (from-to)1462-1469
Number of pages8
JournalChemical Science
Volume4
Issue number4
DOIs
StatePublished - Mar 4 2013

ASJC Scopus subject areas

  • Chemistry(all)

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    Iehl, J., Frasconi, M., Jacquot De Rouville, H. P., Renaud, N., Dyar, S. M., Strutt, N. L., Carmieli, R., Wasielewski, M. R., Ratner, M. A., Nierengarten, J. F., & Stoddart, J. F. (2013). π-Dimerization of viologen subunits around the core of C60from twelve to six directions. Chemical Science, 4(4), 1462-1469. https://doi.org/10.1039/c3sc22250k