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Updated: Apr 23, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
π aromaticity and three-dimensional aromaticity: two sides of the same coin?
Jordi Poater1, Miquel Solà, Clara Viñas
1Department of Theoretical Chemistry and Amsterdam Center for Multiscale Modeling, Vrije Universiteit, De Boelelaan 1083, 1081HV Amsterdam (The Netherlands).
Abstract:
A bridge between classical organic polycyclic aromatic hydrocarbons (PAH) and closo borohydride clusters is established by showing that they share a common origin regulated by the number of valence electrons in an electronic confined space. Application of the proposed electronic confined space analogy (ECSA) method to archetypal PAHs leads to the conclusion that the 4n+2 Wade-Mingos rule for three-dimensional closo boranes is equivalent to the (4n+2)π Hückel rule for two-dimensional PAHs. More importantly, use of ECSA allows design of new interesting fused closo boranes which can be a source of inspiration for synthetic chemists.
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