Evidence for σ Dimerization During Anodic Redox Switching of 1,3,5-Tripyrrolidinobenzene: A New Molecular Switch

1,3,5-tripyrrolidinobenzene is the first example of an aromatic amine that forms σ dimers during oxidation/reduction cycles [Eq. (1); X−=ClO4−], and thus turns out to be an efficient molecular switch. Surprisingly, such σ dimers are relatively stable intermediates during the formation of conjugated oligomers and polymers.