Our working hypothesis to design stable and isolable neutral homoaromatics emanated from elassovalene 3 (Fig. , bottom). Extending the bridging unit from a semibullvalene to a barbaralane core as in 5, we anticipated that an additional carbon atom in the bridge would allow for more structural flexibility and thus would facilitate the interaction of both ends of the -system through-space to allow for homoconjugative interaction . At the same time, the target molecule would in principle bear both a potential 6 as well as a 10 homoaromatic system, allowing to probe larger homoaromatic interactions.