Supramolecular Tilt Chirality Derived from Symmetrical Benzene Molecules: Handedness of the 21 Helical Assembly

Abstract

Achiral molecules can form aggregates with chirality. This depends on the relative position of the molecules, in other words, the tilt of the molecules (so-called supramolecular tilt chirality). In this paper, we describe supramolecular chirality appearing in a 2(1) column composed of symmetrical benzene molecules, which is formed in the host cavity of inclusion crystals of cholic acid. Moreover, we determined the handedness, that is, right or left, of the 2(1) helical column of benzene on the basis of the molecular tilt. Determination of the 2(1) helical handedness was performed on assemblies of other benzene derivatives in cholic acid crystals and benzene assemblies in other host frameworks selected from the Cambridge Structural Database. Finally, we demonstrated complementarity of the handedness between the 2(1) symmetrical host framework of cholic acid and the benzene column.