The synthesis of six tetrathia–oligothiophene macrocycles is described with modest ring-closing yields between 21 and 55%. Single-crystal X-ray studies of four of the macrocycles indicated that encapsulated solvent or guest molecules were possible. A variety of guest molecules were explored for inclusion complexes via NMR, absorption, emission, and X-ray techniques. The solution-phase inclusion complexes were uninformative; yet the solid-state experiments revealed that solvent exchangeable channels exist through the macrocyclic pores.