Issue 4, 2013

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Dec 2012
Accepted
31 Jan 2013
First published
31 Jan 2013

Chem. Sci., 2013,4, 1462-1469

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements