A Study of Some Primary Processes in Electropolymerization by Cyclic Voltammetry of Phenyl-Substituted Ethylenes

Tetraphenylethylene, triphenylethylene, stilbene, 1,1 diphenylethylene, and styrene were utilized as model compounds. Cyclic voltammetry in tetrahydrofuran, , showed that the radical anions of these compounds were protonated in this medium and are therefore stronger nucleophiles than polycyclic aromatic hydrocarbons for which similar protonation does not occur. The stability of the initial ionic species produced increased with the number of phenyl substituents in this series of substituted ethylenes. The cyclic voltammetric data was examined critically to determine the reversibility of the electron transfer steps, the number of electrons added per step, and the stability or lifetime of transient substances formed. Reaction mechanisms are proposed and the relevance of the findings to electropolymerization processes is indicated.