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Fullerene extracts obtained from fullerene soot lack their real application due to their poor solubility in common solvents and difficulty in purification. Encapsulation of these extracts in a suitable host is an important approach to address these issues. We present a new Pd6 barrel (1), which is composed of three 1,4‐dihydropyrrolo[3,2‐b]pyrrole panels, clipped through six cis‐PdII acceptors. Large open windows and cavity make it an efficient host for a large guest. Favorable interactions between the ligand and fullerene (C60 and C70) allows the barrel to encapsulate fullerene efficiently. Thorough investigation reveals that barrel 1 has a stronger binding affinity towards C70 over C60, resulting in the predominant extraction of C70 from a mixture of the two. Finally, the fullerene encapsulated barrels C60⊂1 and C70⊂1 were found to be efficient for visible‐light‐induced singlet oxygen generation. Such preferential binding of C70 and photosensitizing ability of C60⊂1 and C70⊂1 are noteworthy. [ABSTRACT FROM AUTHOR]