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Updated: Sep 15, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Embedding a Planar Antiaromatic Cyclooctatetraene into a Truxene-Derived Polycyclic Aromatic Hydrocarbon
Simone F Ebel1, Frank Rominger1, Michael Mastalerz1
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
None:
Two contorted, monkey saddle-shaped polycyclic aromatic hydrocarbons (PAHs) with tailored substitution patterns were synthesized to enhance their inversion barriers. Along the way, a chiral, truxene-based PAH featuring a planar cyclooctatetraene (COT) core was discovered and structurally confirmed by X-ray crystallography. Its antiaromatic character and optoelectronic properties were investigated and compared to those of its negatively curved precursor. Deuterium-labeling experiments and DFT calculations provided insights into the formation of the planar COT ring.
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