A novel electron-deficient macrocycle, pillar[6]quinone (P[Q]6), has been synthesized for the first time by both chem. and electrochem. oxidn. of pillar[6]arene, showing clear hexagonal columnar stacking in the solid state. Cathodic voltammetric studies of P[Q]6 revealed that three electrons are injected first, followed by stepwise one-electron redns. [on SciFinder(R)]