The growing demand for flexible electronic devices and hydrogen storage materials has spurred a resurgence of interest in polyaryl hydrocarbons including graphene, acenes, fullerenes, polythiophenes, etc. Indenofluorenes are another polyaryl molecular scaffold that has shown utility in the organic and hybrid materials arena, with polymers incorporating the indeno[1,2-b]fluorene moiety being common in organic light emitting diodes. This review examines the syntheses and properties of the five distinct indenofluorene regioisomers, with a focus on small molecule applications in organic electronics of this intriguing and somewhat underexplored family of polyaryl hydrocarbons.