Divergent Synthesis of Molecular Winch Prototypes

Yohan Gisbert (1) , Seifallah Abid (1) , Claire Kammerer (1) , Gwénaël Rapenne (1, 2)

1 CEMES-GNS - Groupe NanoSciences
2 Nara Institute of Science and Technology

We report the synthesis of conceptually new prototypes of molecular winches with the ultimate aim to investigate the work performed by a single ruthenium-based molecular motor anchored on a surface by probing its ability to pull a load upon electrically-driven directional rotation. According to a technomimetic design, the motor was embedded in a winch structure, with a long flexible polyethylene glycol chain terminated by an azide hook to connect a variety of molecular loads. The structure of the motor was first derivatized by means of two sequential cross-coupling reactions involving a penta(4-halogenophenyl)cyclopentadienyl hydrotris(indazolyl)borate ruthenium(II) precursor and the resulting benzylamine derivative was next exploited as key intermediate in the divergent synthesis of a family of nanowinch prototypes. A one-pot method involving sequential peptide coupling and Cu-catalyzed azide-alkyne cycloaddition was developed to yield four loaded nanowinches, with load fragments encompassing triptycene, fullerene and porphyrin moieties.

Mots clés: fullerene; molecular machine; molecular winch; porphyrin; triptycene

Domaines: Chimie de coordination

Yohan Gisbert, Seifallah Abid, Claire Kammerer, Gwénaël Rapenne. Divergent Synthesis of Molecular Winch Prototypes. Chemistry - A European Journal, 2021, 27 (65), pp.16242-16249. ⟨10.1002/chem.202103126⟩. ⟨hal-03636845⟩