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Article Dans Une Revue Chemistry - A European Journal Année : 2023

A Cyclotriveratrylene Solvent‐Dependent Chiral Switch

Louise Miton
  • Fonction : Auteur
Élise Antonetti
Diego García-López
  • Fonction : Auteur
Paola Nava
Vincent Robert
  • Fonction : Auteur
Muriel Albalat
Alexandre Martinez
Yoann Cotelle

Résumé

Abstract Chiral molecular switches are attracting attention as they could pave the way to chiral molecular machines. Herein, we report on the design and synthesis of a single molecule chiral switch based on a cyclotriveratrylene scaffold, in which the chirality inversion is controlled by the solvent. Hemicryptophanes are built around a C 3 cyclotriveratrylene chiral unit, with either M or P handedness, connected to another tripod and usually displaying an “out” configuration. Here, we demonstrate that solvents are able to control the “in” and “out” configurations of the CTV unit, creating a chiral molecular switch from ( M / P )”in” to ( P / M )”out” handedness. The full characterization of the “in” and “out” configurations and of the chirality switch were made possible by combining NMR, HPLC, ECD, DFT and molecular dynamics. Interestingly, bulky aromatic solvents such as 2‐ t ‐butylphenol favor the “in” configuration while polar aprotic solvents such as acetone favor the “out” configuration. This chiral switch was found to be fully reversible allowing the system to oscillate between two different M and P configurations several times upon the action of solvents stimuli.

Domaines

Chimie

Dates et versions

hal-04382458 , version 1 (09-01-2024)

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Paternité

Identifiants

Citer

Louise Miton, Élise Antonetti, Diego García-López, Paola Nava, Vincent Robert, et al.. A Cyclotriveratrylene Solvent‐Dependent Chiral Switch. Chemistry - A European Journal, 2023, ⟨10.1002/chem.202303294⟩. ⟨hal-04382458⟩
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