ChemInform Abstract: ELECTROCHEMICAL AND SPECTROSCOPIC PROPERTIES OF CATION RADICALS PART 3, REACTION PATHWAYS OF CARBAZOLIUM RADICAL IONS

Carbazole electrochemistry: a short review

“…This can be explained by steric hindrance, as this molecule is twisted (not planar), so the N-phenyl and carbazole orbitals are not sufficiently conjugated. This has been confirmed by numerous results from QM calculations [2]. The oxidation potential of 9-phenylcarbazole is not very sensitive to substituents at the para position on the 9-phenyl group, but is of course very sensitive to any substituent at the 3-or 6-position on the carbazole [31].…”

“…Ambrose reports that the oxidation potential depends slightly on the characteristics of the substituent, as shown in Table 1 [2]. Electrochemical oxidation occurs in exactly the same way as for carbazole but leads only to 3,3′-bicarbazyl.…”

“…N-substituted carbazoles generally behave in a similar way to pure carbazole, although there are some exceptions [2,[15][16][17][18][19]. Ambrose reports that the oxidation potential depends slightly on the characteristics of the substituent, as shown in Table 1 [2].…”

“…The former product is usually favored and only a small amount of the 6-6′ product is obtained, but the latter is produced in excess in the presence of a deprotonating species (see Fig. 6) [2]. It is obvious that the oxidation of 3-substituted-N-alkyl carbazoles will only give the 6,6′-dicarbazyl.…”

“…The most recent review of carbazole electrochemistry was actually published a rather long time ago; indeed, no such review appears to have been provided since the work of Ambrose and Nelson [1,2]. Therefore, in this paper we have collated information on the oxidation of carbazole and its derivatives from various sources.…”