Zhou J, Rieker A, Grösser T, Skiebe A, Hirsch A (1997)
Publication Type: Journal article, Original article
Publication year: 1997
Original Authors: Zhou J., Rieker A., Grösser T., Skiebe A., Hirsch A.
Pages Range: 1-5
Journal Issue: 1
URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-0011108599&origin=inward
The electrochemical properties of four singly bridged (1-4) and one doubly bridged (5) N-substituted imino[60]fullerenes have been investigated with cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The substituents on the imino nitrogen are methoxycarbonylmethyl (1, 2, 5), 4-(pentafluorophenoxycarbonyl)phenyl (3), and 4-(succinimidoxycarbonyl)phenyl (4). [6,6]-Bridged structures (2) with closed and [5,6]-bridged structures (1, 3, 5) with open transannular bonds were compared for the first time. Whereas C and 1-4 exhibit four successive, reversible reduction peaks in terms of an EEEE mechanism, a chemical reaction followed the cathodic reduction of 5 to 5. This effect is particularly clear in the DPV, where all subsequent reduction peaks were doubled. This can be explained by an ECEEE mechanism, in which 5 after the first E reduction undergoes a chemical transformation into one or two new species, which are further reduced in EEE processes. In the anodic oxidation of 1-5 a two-electron transfer was confirmed. In sharp contrast to all other fullerene derivatives, a quasireversible oxidation of 4 could be observed. To our knowledge, this is the first report of a quasireversible electrochemical oxidation for C mono adducts. The reduction potentials exhibit good linear relationships with the calculated LUMO energy levels. Significantly, compared to C, the reductions of the [6,6]-bridged derivative 2 as well as of the doubly [5,6]-bridged compound 5 occur at more negative potentials, whereas those of the singly [5,6]-bridged compounds 1,3,4 are found at less negative potentials.
APA:
Zhou, J., Rieker, A., Grösser, T., Skiebe, A., & Hirsch, A. (1997). Electrochemical investigations of singly and doubly bridged imino[60]fullerenes. Journal of the Chemical Society, Perkin Transactions 2, 1, 1-5.
MLA:
Zhou, Jinkou, et al. "Electrochemical investigations of singly and doubly bridged imino[60]fullerenes." Journal of the Chemical Society, Perkin Transactions 2 1 (1997): 1-5.
BibTeX: Download