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Article Dans Une Revue Chemistry - A European Journal Année : 2021

Carbo‐mer of barrelene: a rigid 3D‐carbon‐expanded molecular barrel

Résumé

After extensive studies of 1D and 2D skeletal carbo‐mers based on C8π‐conjugatingdialkynylbutatriene units(DABs: ~C≡C–(R)C=C=C=C(R)–C≡C~) bridging spor sp2centers in carbo‐butene, ‐xylylene or ‐benzene derivatives, 3D versions are envisaged through carbo‐barrelenes and partially reduced derivatives thereofwhere two or three DAB blades span a bridge between sp3carbinol vertices or ether thereof. For R = Ph, stable representatives were synthesized through a pivotal [6]pericyclynedione, and extensively characterized by spectroscopic, electrochemical and crystallographic methods. Density functional theory calculations allow detailed analysis of structural and electronic features of the 7 Å high barrel‐shaped molecules, and show that they can behave as cages for ionic species. Beyond aesthetical concerns, the results could open prospects of applications in host‐guest supramolecular chemistry and single molecule charge transport.
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Dates et versions

hal-03228886 , version 1 (18-05-2021)

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Citer

Chongwei Zhu, Albert Poater, Carine Duhayon, Brice Kauffmann, Alix Saquet, et al.. Carbo‐mer of barrelene: a rigid 3D‐carbon‐expanded molecular barrel. Chemistry - A European Journal, 2021, 27 (36), pp.9286-9291. ⟨10.1002/chem.202100670⟩. ⟨hal-03228886⟩
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