Giant Cyclophanes Built from Polyphenyl Aromatic Substructures

Abstract

Two very large cyclophanes (3, C₁₃₂H₉₂O₈S₄; 4, C₁₇₂H₁₂₀O₈S₄) were prepared by means of short syntheses (∼5 steps) from commercial starting materials. In each of these cyclophanes, two octaphenylnaphthalene subunits or two 1,3-bis(pentaphenylphenyl)benzene subunits were tethered to form the final macrocycle. X-ray analysis of 3 shows it to have a collapsed conformation, but molecules of 4 have large central cavities which are aligned in the crystal to form wide, solvent-containing channels.