Of the five possible indenofluorene regioisomers, examples of afully conjugated indeno[1,2-a]fluorene scaffold have so far remained elusive.This work reports the preparation and characterization of 7,12-dimesitylindeno[1,2-a]fluorene as ahighly reactive species.Experimental and computational data support the notion of am olecule with pronounced diradical character that exists in at riplet ground state.A ss uch, both NICS and ACID calculations suggest that the indeno[1,2a]fluorene scaffold is weakly Baird aromatic.Reduction of the unstable red solid with Cs metal produces the dianion of the title compound, from which single crystals could be obtained and X-raydata acquired, thus fully corroborating the proposed indeno[1,2-a]fluorene hydrocarbon core.