Synthesis and Properties of Indeno[2,1-c]fluorenes and Benzo- Fused Analogues

Abstract : A new 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 show 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.
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Tanguy Jousselin-Oba, Parker Deal, Aaron Fix, Conerd Frederickson, Chris Vonnegut, et al.. Synthesis and Properties of Indeno[2,1-c]fluorenes and Benzo- Fused Analogues. Chemistry - An Asian Journal, Wiley-VCH Verlag, 2018, 14 (10), pp.1737-1744. ⟨10.1002/asia.201801684⟩. ⟨hal-02353560⟩

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