Structural Characterization of Thiocyclophanes That Promote Edge-to-Face Aromatic-Aromatic Geometries

Article abstract of DOI:10.1021/jo00118a030

Several <4.4>thiocyclophanes have been examined in solution and the solid state.These molecules contain two aromatic units, phenyl and/or naphthyl, with linking chains attached meta or para on the phenyl groups, and 1,3 or 1,4 on the naphthyl groups.Most previous studies of cyclophanes containing two aromatic rings have focused on enforcing parallel alignment of those rings.The molecules discussed here, in contrast, were chosen to promote edge-to-face juxtapositions.Crystallographic data confirm that edge-to-face orientations between the linked aromatic groups are available for these cyclophanes, and 1H NMR data indicate that conformations containing these orientations are populated in solution.These cyclophanes provide spectroscopic references for NMR-based studies of folding in more flexible diphenyl and dinaphthyl compounds.