Planar Tetraindolodipleiadiene via Zirconium-Promoted Intramolecular Indolyl C4-H Homocoupling.

A novel N-rimmed PAH molecule containing a dipleiadiene core ( TIDP ) was designed and synthesized from indole, wherein a ZrCl 4 -promoted intramolecular C4-H homocoupling reaction of the indole moieties was the key approach. TIDP exhibited a nearly full planar structure and antiaromaticity of the two embedded heptagonal rings. The extremely stable radical cation TIDP •+ ·PF 6 - was isolated quantitatively by oxidation with AgPF 6 .