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A set of fully‐conjugated indenofluorenes has been synthesized and confirmed by solid‐state structure analysis. The indeno[2,1‐c]fluorenes and their benzo‐fused analogues all contain the antiaromatic as‐indacene core. The molecules possess high electron affinities and show a broad absorption that reaches into the near‐IR region of the electromagnetic spectrum. All of the featured compounds reversibly accept up to two electrons as revealed by cyclic voltammetry. Analysis of molecule tropicity using NICS‐XY scan calculations shows that, while the as‐indacene core is less paratropic than s‐indacene, benz[a]‐annulation further reduces the antiaromaticity of the core. Antiaromatic strength of the as‐indacene core can also be tuned by the position of fusion of additional arenes on the outer rings.