Treatment of cycloparaphenylene (CPP) with the oxidant triethyloxonium hexachloroantimonate afforded an isolable radical cation of the parent carbon nanohoop. The photophysical properties of CPP˙+SbCl6− were investigated, showing the presence of two absorptions at 535 nm and 1115 nm. Time-dependent density functional theory (DFT) calculations were used to examine these optical absorptions, revealing a delocalized, quinoidal carbon nanohoop. Upon mixing with neutral cycloparaphenylene, the formation of an unusually strong charge-resonance complex (CPP2)˙+ was observed. Spectroscopic and computational studies were indicative of extensive intermolecular charge delocalization between the two carbon nanohoops as well.