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Issue 4, 2013
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π-Dimerization of viologen subunits around the core of C60 from twelve to six directions

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Abstract

Molecular reorganization around the core of C60 has been achieved by electron transfer centered on π-dimerizable viologen subunits located in a restricted region of space. Fullerene C60 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 π-dimers. Theoretical calculations reveal that the close proximity of the orbitals of the viologen subunits attached to the C60 facilitate 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 C60 can be controlled electrochemically using noncovalent reversible interactions.

Graphical abstract: π-Dimerization of viologen subunits around the core of C60 from twelve to six directions

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Article information


Submitted
16 Dec 2012
Accepted
31 Jan 2013
First published
31 Jan 2013

Chem. Sci., 2013,4, 1462-1469
Article type
Edge Article

π-Dimerization of viologen subunits around the core of C60 from twelve to six directions

J. Iehl, M. Frasconi, H. Jacquot de Rouville, N. Renaud, S. M. Dyar, N. L. Strutt, R. Carmieli, M. R. Wasielewski, M. A. Ratner, J. Nierengarten and J. F. Stoddart, Chem. Sci., 2013, 4, 1462
DOI: 10.1039/C3SC22250K

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