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Tytuł:
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Stereoselective Syntheses, Structures, and Properties of Extremely Distorted Chiral Nanographenes Embedding Hextuple Helicenes.
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Autorzy:
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Roy, Myriam
Berezhnaia, Veronika
Villa, Marco
Vanthuyne, Nicolas
Giorgi, Michel
Naubron, Jean‐Valère
Poyer, Salomé
Monnier, Valérie
Charles, Laurence
Carissan, Yannick
Hagebaum‐Reignier, Denis
Rodriguez, Jean
Gingras, Marc
Coquerel, Yoann
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Temat:
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HELICENES
DIHEDRAL angles
POLYCYCLIC aromatic hydrocarbons
EMBEDDINGS (Mathematics)
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Źródło:
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Angewandte Chemie; 2/17/2020, Vol. 132 Issue 8, p3290-3297, 8p
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We report a molecular design and concept using π‐system elongation and steric effects from helicenes surrounding a triphenylene core toward stable chiral polycyclic aromatic hydrocarbons (PAHs) with a maximal π‐distortion to tackle their aromaticity, supramolecular and molecular properties. The selective syntheses, and the structural, conformational and chiroptical properties of two diastereomeric large multi‐helicenes of formula C90H48 having a triphenylene core and embedding three [5]helicene units on their inner edges and three [7]helicene units at their periphery are reported based on diastereoselective and, when applicable, enantiospecific Yamamoto‐type cyclotrimerizations of racemic or enantiopure 9,10‐dibromo[7]helicene. Both molecules have an extremely distorted triphenylene core, and one of them exhibits the largest torsion angle recorded so far for a benzene ring (twist=36.9°). [ABSTRACT FROM AUTHOR]
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