Overcrowded Triply Fused Carbo[7]helicene

Albert Artigas (1) , Florian Rigoulet (1) , Michel Giorgi (2) , Denis Hagebaum-Reignier (1) , Yannick Carissan (1) , Yoann Coquerel (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 FSCM - Fédération des Sciences Chimiques de Marseille

This paper presents the synthesis and comprehensive analysis of a highly contorted and doubly negatively curved multihelicene compound, composed of three carbo[7]helicene units fused within a central six-membered ring. The synthesis of this compound involved a [2 + 2 + 2] cycloaddition reaction of 13,14-picyne, employing a Ni(0) catalyst, which exhibited superior performance compared to conventional Pd(0) catalysts. The evaluation of aromaticity in this triple carbo[7]helicene, utilizing magnetic and electronic criteria, led to noteworthy insights challenging the limitations of Clar’s model of aromaticity.

Mots clés: Aromatic compounds; Aromaticity; Chemical structure; Cyclization; Molecules

Domaines: Chimie organique

Albert Artigas, Florian Rigoulet, Michel Giorgi, Denis Hagebaum-Reignier, Yannick Carissan, et al.. Overcrowded Triply Fused Carbo[7]helicene. France. 2023. ⟨hal-04413916⟩