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

Takao Fujikawa, Dorin V. Preda, Yasutomo Segawa, Kenichiro Itami, and Lawrence T. Scott

Org. Lett. 2016, 18, 3992-3995. DOI: 10.1021/acs.orglett.6b01801

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.

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