Carbo-mer of Barrelene: A Rigid 3D-Carbon-Expanded Molecular Barrel |
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Authors: | Dr. Chongwei Zhu Dr. Albert Poater Dr. Carine Duhayon Dr. Brice Kauffmann Dr. Alix Saquet Dr. Arnaud Rives Dr. Valérie Maraval Prof. Remi Chauvin |
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Affiliation: | 1. LCC-CNRS, University of Toulouse, 205 route de Narbonne, 31077 Toulouse, France;2. Institut de Química Computacional i Catàlisi and, Departament de Química, Universitat de Girona, c/ Maria Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain;3. CNRS, INSERM, UMS3033/US001, Institut Européen de Chimie Biologie, Université de Bordeaux, 33607 Pessac, France |
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Abstract: | After extensive studies of 1D and 2D skeletal carbo-mers based on C8 π-conjugating dialkynylbutatriene units (DABs: ∼C≡C−(R)C=C=C=C(R)−C≡C∼) bridging sp or sp2 centers in carbo-butene, carbo-xylylene or carbo-benzene derivatives, 3D versions are envisaged through carbo-barrelenes and partially reduced derivatives thereof where two or three DAB blades span a bridge between sp3 carbinol 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 C26 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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Keywords: | alkynes barrelenes butatrienes carbo-mer covalent cages |
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