Funktionalisierung von Buckminsterfulleren C<sub>60</sub> durch [8 + 2]‐Cycloaddition: spektroskopische und Elektronentransfereigenschaften eines Tetrahydroazulenofullerens

Beer, Ernst; Feuerer, Michaela; Knorr, Andreas; Mirlach, A.; Daub, Jörg

doi:10.1002/ange.19941061010

Cited by 7 publications

(1 citation statement)

References 19 publications

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“…The electrochemical investigation of C 60 1- 17 and its derivatives [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] has been an interesting subject since the beginning of preparative fullerene research. 35, 36 While the cathodic reduction has received more attention, the anodic oxidation remained largely unexplored.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Zhou¹,

Rieker²,

Grosser³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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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 60 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 Ϫ . 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 60 mono adducts. The reduction potentials exhibit good linear relationships with the calculated LUMO energy levels. Significantly, compared to C 60 , 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.

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Section: Introductionmentioning

confidence: 99%

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Zhou¹,

Rieker²,

Grosser³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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Chromophore‐Appended C ₆₀ and C ₇₀ Fullerenes: Anthracene and Pyrene Derivatives – Syntheses, Cyclic Voltammetry, and Spectra

Gareis

Köthe

Daub³

1998

European J Organic Chem

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Microelectrode Voltammetry for the Study of Pyrrolidinofullerenes

et al. 1999

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The electrochemical behaviors of ®ve pyrrolidinofullerenes containing ester groups have been investigated by cyclic voltammetry on a gold microdisk electrode. Four reversible waves for each fullerene derivatives are observed. The potential values for these four waves differ slightly from one compound to the other. The diffusion coef®cient of these compounds is measured according to their steady-state voltammograms.

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Funktionalisierung von Buckminsterfulleren C₆₀ durch [8 + 2]‐Cycloaddition: spektroskopische und Elektronentransfereigenschaften eines Tetrahydroazulenofullerens

Cited by 7 publications

References 19 publications

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Chromophore‐Appended C ₆₀ and C ₇₀ Fullerenes: Anthracene and Pyrene Derivatives – Syntheses, Cyclic Voltammetry, and Spectra

Microelectrode Voltammetry for the Study of Pyrrolidinofullerenes

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Funktionalisierung von Buckminsterfulleren C60 durch [8 + 2]‐Cycloaddition: spektroskopische und Elektronentransfereigenschaften eines Tetrahydroazulenofullerens

Cited by 7 publications

References 19 publications

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Electrochemical investigations of singly and doubly bridged imino[60]fullerenes

Chromophore‐Appended C 60 and C 70 Fullerenes: Anthracene and Pyrene Derivatives – Syntheses, Cyclic Voltammetry, and Spectra

Microelectrode Voltammetry for the Study of Pyrrolidinofullerenes

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Funktionalisierung von Buckminsterfulleren C₆₀ durch [8 + 2]‐Cycloaddition: spektroskopische und Elektronentransfereigenschaften eines Tetrahydroazulenofullerens

Chromophore‐Appended C ₆₀ and C ₇₀ Fullerenes: Anthracene and Pyrene Derivatives – Syntheses, Cyclic Voltammetry, and Spectra