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Updated: May 18, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Twisted arenes
1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV, 26506-6045, USA, kung.wang@mail.wvu.edu.
Abstract:
The nonbonded steric interactions of substituents at the crowded C4 and C5 positions of phenanthrene cause the aromatic system to twist out of planarity. Similarly, the presence of substituents at the C1 and C12 positions of benzo[c]phenanthrene and at the C1 and C14 positions of dibenzo[c,g]phenanthrene are responsible for the helical twists of the aromatic frameworks. Highly substituted acenes, such as octamethylnaphthalene and decaphenylanthracene, also exhibit substantial end-to-end twists. The X-ray structures of these compounds allow direct measurements of the extent of the structural distortions. The configurational stabilities of many twisted arenes have also been determined.
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