An Electrochemical Investigation into a Series of Tricyanovinylated Pyrrole Moieties

McCormac, Timothy and Farrell, David and Browne, Wesley and Johannes, G. Vos (2004) An Electrochemical Investigation into a Series of Tricyanovinylated Pyrrole Moieties. Electroanalysis, 16 (20). pp. 1682-1689. ISSN 1010-0397

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The electrochemical behaviour of three tri-cyanovinylated pyrrole species namely, 2- tricyanovinyl-pyrrole (C4H4N-C5N3), 2-tricyanovinyl-N-methylpyrrole (C5H6N-C5N3) and 2- tricyanovinyl-N-phenylpyrrole (C10H8N-C5N3), has been studied. All compounds were found to exhibit both an irreversible oxidation at more positive potentials compared to the unsubstituted monomer species and a reversible reduction redox couple associated with reduction of the co-ordinated cyano ligands. The latter reductions of the tricyanovinylated compounds to their radical anions at platinum, carbon and gold electrodes in acetonitrile solution have been studied by cyclic voltammetry, using a variety of supporting electrolytes.The half-wave potentials for each compound were found to be dependent upon the supporting electrolyte but independent of the nature of the electrode surface. This is attributed to ion-pairing between the anions and the alkali metal cations. The reduction based redox processes for the C10H8N-C5N3 and C5H6N-C5N3 compounds were found to be facile in nature and independent of both the nature of the electrolyte and electrode surface. However the reduction of C4H4N-C5N3 was found to be irreversible in nature. Attempts were made to elucidate, by both electrochemical and spectroscopic means, the structure of the products obtained upon oxidation of the tricyanovinylated compounds.

Item Type: Article
Uncontrolled Keywords: Pyrrole; Tricyanovinylated; Heterogeneous rate constants; Irreversible oxidation
Subjects: Science > Chemistry
Research Centres: Electrochemistry Research Group
Depositing User: Nicola Hanlon
Date Deposited: 15 Mar 2011 11:49
Last Modified: 11 Nov 2014 16:09

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