Stable high-order molecular sandwiches: hydrocarbon polyanion pairs with multiple lithium ions inside and out

Stable ten-component sandwich compounds have been characterized in which four lithium ions reside between two tetraanions derived from corannulene or its alkyl-substituted derivatives and four additional lithium ions decorate the exterior. In tetrahydrofuran solution, the four lithium ions inside the sandwich can exchange environments with the four external lithium atoms, but the two tetraanion decks of the sandwich never separate from one another on the time scale of nuclear magnetic resonance. Theoretical calculations point to a "stacked bowl" conformation and a low energy barrier for synchronous double inversion of the tetraanion bowls in the solvated sandwich compounds.