Charged aromatic triangulene derivatives are synthesized. The cationic and anionic derivatives, when mixed together, form aromatic ion-pairs. Strong interactions between the oppositely charged non-Kekul� p-systems are observed in both solid and solution states. The triangulene cations form face-to-face polymers and homodimers in the crystalline state, while the iso-structural anion does not. Differences in visible-near-IR absorption and emission profile of triangulene anion in the presence of different cations shows that the ion-pairing between the aromatic monopoles in solution state is greatly affected by sterics. Observation of strong fluorescence quenching shows formation of ground-state non-fluorescent ion-pairs. The strong interactions are a result of synergy between weak aromatic interactions and strong electrostatic interactions.

Synthesis of triangulene derivatives: Study of ion-pairing in charged triangulenes

246th National Meeting (2013)

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