Amine-Amine Electronic Coupling through a Dibenzo[a,e]pentalene Bridge.

Three dibenzo[a,e]pentalene derivatives containing two redox-active amine substituents have been prepared. The degree of amine-amine electronic coupling through the dibenzo[a,e]pentalene bridge greatly depends on the substitution positions. Three monoamine compounds have been prepared for comparison studies. The experimental data and analysis were corroborated by time-dependent density functional theory results of mixed-valent compounds.