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Issue 7, 2000
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Synthesis and electrochemical behaviour of [60]fullerene possessing poly(arylacetylene) dendrimer addends

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61,61-Bis[4-{3,5-bis(3,5-di-tert-butylphenylethynyl)phenylethynyl}phenyl]-1,2-dihydro-1,2-methano[60]fullerene (10) and 61,61-bis[4-{3,5-bis[3,5-bis(3,5-di-tert-butylphenylethynyl)phenylethynyl]phenylethynyl}phenyl]-1,2-dihydro-1,2-methano[60]fullerene (11) with 1st and 2nd generation phenylacetylene dendrimer addends were synthesised according to the Wudl method. Both monoadducts are obtained as single isomers in 18% and 23% yields, respectively. The structures of the products were established by FTIR, 1H NMR, 13C NMR and UV/VIS spectroscopy, as well as by mass spectrometry. All spectroscopic data confirm the exclusive formation of methano[60]fullerenes with [6,6]-closed structures. The electrochemical and spectroelectrochemical properties of 2nd generation dendrimer 7 and of its fullerene derivative 11 have been investigated. The cyclic voltammetric study shows that no significant interaction occurs in the ground state between the fullerene and the dendrimer; the fullerene derivative retains the typical redox stability of 6,6-closed derivatives in both the cyclic voltammetry (CV) and bulk electrolysis timescales.

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Publication details

The article was received on 17 Mar 2000, accepted on 22 May 2000 and first published on 12 Jun 2000

Article type: Paper
DOI: 10.1039/B002178O
J. Chem. Soc., Perkin Trans. 2, 2000, 1409-1414

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    Synthesis and electrochemical behaviour of [60]fullerene possessing poly(arylacetylene) dendrimer addends

    A. G. Avent, P. R. Birkett, F. Paolucci, S. Roffia, R. Taylor and N. K. Wachter, J. Chem. Soc., Perkin Trans. 2, 2000, 1409
    DOI: 10.1039/B002178O

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