Aniline trimers, just like the polymer polyaniline, exist in three distinct oxidation states - pernigraniline (the most oxidized), emeraldine (intermediate), and leucoemeraldine (the most reduced). The names date from the 19th century.


Aniline trimer in the leucoemeraldine oxidation state

Figure 1 - molecular structure of leucoemeraldine trimer

Aniline trimer in the emeraldine oxidation state

Figure 2 - molecular structure of emeraldine trimer

Aniline trimer in the pernagraniline oxidation state

Figure 3 - molecular structure of pernagraniline trimer

Aniline trimer in the emeraldine oxidation state

Figure 4 - Syn - N, N'-bis(4'aminophenyl)-1,4-quinonediimine (aka emeraldine trimer), optimized at B3LYP/6-31G(d). Hydrogen atoms are white, carbon atoms are cyan, and nitrogen atoms are blue.

emeraldine trimer HOMO's and LUMO's

pernigraniline timer HOMO's and LUMO's

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