Corannulene–Helicene Hybrids: Chiral π‑Systems Comprising Both Bowl and Helical Motifs

Two
distinct structural elements that render π-systems nonplanar,
i.e., geodesic curvature and helical motifs, have been combined into
new polyarenes that contain both features. The resultant corannulene–[n]­helicenes (n = 5, 6) show unique molecular
dynamics in their enantiomerization processes, including inversion
motions of both the bowl and the helix. Optical resolution of a corannulene-based
skeletally chiral molecule was also achieved for the first time, and
the influence of the bowl-motif annulation on the chiroptical properties
was investigated.