Stabilization of a 12-π electrons diamino-benzoquinonediimine tautomer.

The first example of diamino-benzoquinonediimine bearing both electron-donating and electron-withdrawing groups on the same 6-π electron subunit was synthesized using a straightforward one pot strategy. Photophysical analysis and theoretical calculations demonstrate that this unique substitution pattern is efficient to favour the establishment of a single tautomeric structure in solution.