Homoaromatic molecules display characteristics of aromatic stabilization yet possess an interrupted cyclic conjugated -system . The concept of homoaromaticity, resting upon through-bond or through-space homoconjugation (the interaction between disconnected -systems, usually interrupted by one or more sp -hybridized carbon atoms ) has been highly controversial in the past . The difficulty to identify clear criteria for the assignment of molecules as homoaromatic at first as well as the small number of known homoaromatic molecules further spurred the discussion in this field.