With the recent surge of interest in novel conjugated aromatic systems for organic electronic applications, many new molecules based on the indenofluorene scaffold have been synthesized. While many derivatives like fluoreno[4,3-c]fluorene or the diindenothienothiophenes have examined the possibility of expanding the dearomatized core, no work has studied the effect of expanding the conjugation on the outer rings. We are examining the effect of extending the outer conjugation by the preparation of three dinapthoindacene isomers. These compounds allow quick access to optoelectronic properties similar to the expanded fluorenofluorene core including a red shifted absorbance when compared to the indeno[1,2-b]fluorene and two reversible reductions. Results to date show that these molecules, which are a seven-ring fused system with an anti-aromatic core, are remarkably stable and arrange themselves in promising motifs in the sold state.