Abstract
The gold-catalyzed synthesis of an unsymmetrical phenanthreno-benzopentalene derivative is reported. The molecule is characterized experimentally by NMR spectroscopy, X-ray crystallography, UV–Vis spectroscopy and cyclic voltammetry. The experimental results are further confirmed by theoretical studies, including the calculation of aromaticity indices (NICS, ACID). The results show that vertical π-extension of dibenzo[a,e]pentalene through formal benzene ring fusions contributes to increased antiaromaticity relative to linear fusion of the same number of benzene rings. This further confirms that antiaromaticity within a polycyclic conjugated system could be efficiently tuned via the nature of the π-system that is fused to the antiaromatic subunit.
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