Loading Linear Arrays of CuII Inside Aromatic Amide Helices

Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18461-18466. doi: 10.1002/anie.202104734. Epub 2021 Jul 1.

Abstract

The very stable helices of 8-amino-2-quinolinecarboxylic acid oligoamides are shown to uptake CuII ions in their cavity through deprotonation of their amide functions with minimal alteration of their shape, unlike most metallo-organic structures which generally differ from their organic precursors. The outcome is the formation of intramolecular linear arrays of a defined number of CuII centers (up to sixteen in this study) at a 3 Å distance, forming a molecular mimic of a metal wire completely surrounded by an organic sheath. The helices pack in the solid state so that the arrays of CuII extend intermolecularly. Conductive-AFM and cyclic voltammetry suggest that electrons are transported throughout the metal-loaded helices in contrast with hole transport observed for analogous foldamers devoid of metal ions.

Keywords: CuII coordination; electron transport; helix; metallofoldamers; self-assembled monolayers.

Publication types

  • Research Support, Non-U.S. Gov't