Electroreduction of 9-fluoro-10-cyanoanthracene

Heınze, Jürgen; Rasche, Armin

doi:10.1016/s1388-2481(03)00180-2

Cited by 3 publications

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“…The reversible self-association or coupling of π-conjugated radical ions has been observed by numerous research groups, e.g. for radical anions of 9-fluoro-10-cyanoanthracene ( FCA •– ) and 9-cyanoanthracene as well as for radical cations of octamethylbiphenylene ( OMB •+ ) and alkylated oligothiophenes. − The formation of dimers in these reports was proven by the concentration- and temperature-dependence of cyclic voltammetric (CV) measurements, electron paramagnetic resonance (EPR), and UV/vis spectra. In the case of radical anions, the formation of σ-dimers has been widely accepted, whereas π or σ-dimerization are discussed in the case of radical cations.…”

Section: Introductionmentioning

confidence: 95%

Electrochemically Induced Reversible and Irreversible Coupling of Triarylamines

et al. 2011

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The electrochemical coupling and dimerization behavior of the low molecular compounds triphenylamine (TPA) and 9-phenylcarbazole (PHC) in comparison to tri-p-tolylamine (p-TTA) with para-blocked methyl groups has been investigated in detail. In contrast to the unsubstituted radical cations of TPA and PHC, the radical cations of p-TTA are stable in the radical cation state and do not undergo any further coupling reactions. However, we found that the dicationic state of p-TTA does undergo two different competitive reaction pathways: (1) an irreversible intramolecular coupling reaction which leads to phenylcarbazole moieties and (2) a reversible intermolecular dimerization leading to charged σ-dimers. The σ-dimers become decomposed upon discharging at low potentials (E(pc) = -0.97 V vs Fc/Fc(+)) so that the starting monomer p-TTA is partially regenerated. In particular, the reversible dimerization reaction has not been described in literature so far. Polymeric systems containing para-methyl blocked triarylamines in the side chain exhibit similar coupling behavior upon electrochemical doping.

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