A Chemically and Electrochemically Switchable [2]Catenane Incorporating a Tetrathiafulvalene Unit

Masumi Asakawa, Peter R. Ashton, Vincenzo Balzani, Alberto Credi, Christoph Hamers, Gunter Mattersteig, Marco Montalti, Andrew N. Shipway, J. Fraser Stoddart, Malcolm S. Tolley,

Angewandte Chemie International Edition · 1998 · 336 citations · 0 references

Concepts

Abstract

A mechanical switch in a [2]catenane, made up of a cyclobis(paraquat-p-phenylene) tetracation interlocked with a macrocyclic polyether containing a redox-active tetrathiafulvalene (TTF) unit and a 1,5-dioxynaphthalene ring system, can be thrown either chemically or electrochemically. The neutral TTF unit resides “inside” the tetracationic cyclophane in the reduced state and “alongside” it in the oxidized species (TTF+/ TTF2+). Switching between the reduced (I4+) and oxidized state (I5+(I6+)) is accompanied by a dramatic color change.