Acid-base controlled multiple conformation and aromaticity switches in tren-capped hexaphyrins

Stéphane Le Gac (1) , Elsa Caytan (1) , Vincent Dorcet (1) , Bernard Boitrel (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Upon protonation, a tren-capped hexaphyrin undergoes successive rectangular-to-Möbius and Möbius-to-triangular conformational isomerizations, with concomitant antiaromaticity-to-aromaticity reversal. This affords different cage environments leading ultimately to a "crypto-bowl-shape" hexaphyrin hosting a trifluoroacetate counterion.

Domaines: Chimie organique; Chimie théorique et/ou physique

Stéphane Le Gac, Elsa Caytan, Vincent Dorcet, Bernard Boitrel. Acid-base controlled multiple conformation and aromaticity switches in tren-capped hexaphyrins. Organic & Biomolecular Chemistry, 2019, 17 (15), pp.3718-3722. ⟨10.1039/c9ob00489k⟩. ⟨hal-02087814⟩