Indeno[1,2-]fluorenes (IFs), while containing 4n π-electrons, are best described as two aromatic benzene rings fused to a weakly paratropic -indacene core. In this study, we find that replacement of the outer benzene rings of an IF with benzothiophenes allows the antiaromaticity of the central -indacene to strongly reassert itself. Herein we report a combined synthetic, computational, structural, and materials study of and indacenodibenzothiophenes (IDBTs). We have developed an efficient and scalable synthesis for preparation of a series of aryl- and ethynyl-substituted IDBTs. NICS-XY scans and ACID calculations reveal an increasingly antiaromatic core from [1,2-]IF to IDBT, with IDBT being nearly as antiaromatic as the parent indacene. As an initial evaluation, the intermolecular electronic couplings and electronic band structure of a diethynyl IDBT derivative reveal the potential for hole and / or electron transport. OFETs constructed using this molecule show the highest hole mobilities yet achieved for a fully conjugated IF derivative.