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Image (Illustration) Année : 2020

Stereoselective Syntheses, Structures, and Properties of Extremely Distorted Chiral Nanographenes Embedding Hextuple Helicenes

Laurence Charles
Jean Rodriguez
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  • PersonId : 921781
  • IdRef : 260692638

Résumé

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°).

Mots clés

Domaines

Chimie organique

Dates et versions

hal-02990017 , version 1 (05-11-2020)

Licence

Domaine public

Identifiants

  • HAL Id : hal-02990017 , version 1

Citer

Myriam Roy, Veronika Berezhnaia, Marco Villa, Nicolas Vanthuyne, Michel Giorgi, et al.. Stereoselective Syntheses, Structures, and Properties of Extremely Distorted Chiral Nanographenes Embedding Hextuple Helicenes. Illustration. France. 2020. ⟨hal-02990017⟩
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