π-Dimerization of viologen subunits around the core of C60 from 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

Research output: Contribution to journalArticle

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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 C 60 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.

Original languageEnglish
Pages (from-to)1462-1469
Number of pages8
JournalChemical Science
Volume4
Issue number4
DOIs
Publication statusPublished - 2013

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Viologens
Dimerization
Bearings (structural)
Carbon
Alkynes
Azides
Cycloaddition
Dimers
Paramagnetic resonance
Copper
Direction compound
Electrons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Iehl, J., Frasconi, M., Jacquot De Rouville, H. P., Renaud, N., Dyar, S. M., Strutt, N. L., ... Stoddart, J. F. (2013). π-Dimerization of viologen subunits around the core of C60 from twelve to six directions. Chemical Science, 4(4), 1462-1469. https://doi.org/10.1039/c3sc22250k

π-Dimerization of viologen subunits around the core of C60 from twelve to six directions. / Iehl, Julien; Frasconi, Marco; Jacquot De Rouville, Henri Pierre; Renaud, Nicolas; Dyar, Scott M.; Strutt, Nathan L.; Carmieli, Ranaan; Wasielewski, Michael R; Ratner, Mark A; Nierengarten, Jean François; Stoddart, J. Fraser.

In: Chemical Science, Vol. 4, No. 4, 2013, p. 1462-1469.

Research output: Contribution to journalArticle

Iehl, J, Frasconi, M, Jacquot De Rouville, HP, Renaud, N, Dyar, SM, Strutt, NL, Carmieli, R, Wasielewski, MR, Ratner, MA, Nierengarten, JF & Stoddart, JF 2013, 'π-Dimerization of viologen subunits around the core of C60 from twelve to six directions', Chemical Science, vol. 4, no. 4, pp. 1462-1469. https://doi.org/10.1039/c3sc22250k
Iehl J, Frasconi M, Jacquot De Rouville HP, Renaud N, Dyar SM, Strutt NL et al. π-Dimerization of viologen subunits around the core of C60 from twelve to six directions. Chemical Science. 2013;4(4):1462-1469. https://doi.org/10.1039/c3sc22250k
Iehl, Julien ; Frasconi, Marco ; Jacquot De Rouville, Henri Pierre ; Renaud, Nicolas ; Dyar, Scott M. ; Strutt, Nathan L. ; Carmieli, Ranaan ; Wasielewski, Michael R ; Ratner, Mark A ; Nierengarten, Jean François ; Stoddart, J. Fraser. / π-Dimerization of viologen subunits around the core of C60 from twelve to six directions. In: Chemical Science. 2013 ; Vol. 4, No. 4. pp. 1462-1469.
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