Synthesis, structure, and chirality of hydroxyl- and carboxyl-functionalized cubane-like photodimers of 2-naphthalene

Two novel hydroxyl- and carboxyl-functionalized cubane-like photodimers from methyl 2-naphthoate have been successfully achieved under mild conditions. X-ray crystal structures confirm that the cubane-like structure is well retained in these two derivatives and the intermolecular Osingle bondH⋯O hydrogen bonding plays an important role in crystal packing. It is of significance that the isolated racemic mixture can be subsequently resolved into two optically pure enantiomers by high-performance liquid chromatography.