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Carbo ‐mer of Barrelene: A Rigid 3D‐Carbon‐Expanded Molecular Barrel
Author(s) -
Zhu Chongwei,
Poater Albert,
Duhayon Carine,
Kauffmann Brice,
Saquet Alix,
Rives Arnaud,
Maraval Valérie,
Chauvin Remi
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100670
Subject(s) - supramolecular chemistry , barrel (horology) , molecule , chemistry , crystallography , density functional theory , ether , benzene , electrochemistry , materials science , stereochemistry , computational chemistry , organic chemistry , composite material , electrode
After extensive studies of 1D and 2D skeletal carbo ‐mers based on C 8 π‐conjugating dialkynylbutatriene units (DABs: ∼C≡C−(R)C=C=C=C(R)−C≡C∼) bridging sp or sp 2 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 sp 3 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 C 26 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.