A rigid octacationic tetraviologen-based cyclophane, (8+), is reported. It possesses a highly electron-deficient rectangular cavity with a length of 23 Å and width of 6.1 Å and is capable of encapsulating either two small π-aromatic guest molecules, such as PhMe and PhCl, simultaneously, or one large molecule, e.g., bis-1,5-dinaphtho[50]crown-14.