2012
DOI: 10.1002/chem.201201264
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A Molecular Shuttle Driven by Fullerene Radical‐Anion Recognition

Abstract: We describe a electrochemically driven molecular shuttle, in which shuttling takes place by means of fullerene radical-anion recognition that results in a very low operation potential (E(1/2) =-0.580 V vs. decamethylferrocene). This has been achieved by introducing positive charges on the macrocycle, which strengthen the existing π-π interactions between the macrocycle and the electrogenerated fullerene radical anion by means of an electrostatic component. In addition, the synthesis of such a molecular shuttle… Show more

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Cited by 33 publications
(18 citation statements)
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“…Electrochemical experiments were carried out in an airtight single-compartment cell described elsewhere, using platinum and silver spirals, respectively, as counter and quasi-reference electrodes44. The E 1/2 values, reported in the Ag/AgCl/KCl (3 M) scale, have been determined by adding decamethylferrocene as an internal standard at the end of each experiment.…”
Section: Methodsmentioning
confidence: 99%
“…Electrochemical experiments were carried out in an airtight single-compartment cell described elsewhere, using platinum and silver spirals, respectively, as counter and quasi-reference electrodes44. The E 1/2 values, reported in the Ag/AgCl/KCl (3 M) scale, have been determined by adding decamethylferrocene as an internal standard at the end of each experiment.…”
Section: Methodsmentioning
confidence: 99%
“…Its incorporation into these potentially machine-like structures could give rise to a series of electrochemically induced events such as electron transfer, acting in the sense of para-carborane or C 60 in a new kind of electroactive dyad. 52,53 However, we wanted to see if its redox and optical properties changed because of the intramolecular interactions present in the molecule.…”
Section: Zwitterion E-[11]mentioning
confidence: 99%
“…A gradual decrease in the second reduction potential with a decrease in the length of the alkyl spacer indicates the importance of the proximity of the fullerene and phthalimide moieties and could be a consequence of noncovalent interactions bewww.eurjoc.org tween the fulleride anion and the electron-accepting phthalimide moiety. [10,17,28,[30][31][32] The linear relationship existing between peak current and the square root of the scan rate between 0.01-1 V s -1 (correlation coefficient about 0.99) shows that the electrochemical processes are predominantly diffusion controlled in the entire scan rate range studied. The third and fourth reduction peaks are overlapping and belong to the reductions of NBP and NMF (-2.02 and -2.05 V, respectively).…”
Section: Electrochemical Studymentioning
confidence: 88%