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; Neil Spencer; J Fraser Stoddart; Malcolm S Tolley; Margherita Venturi; Andrew J P White; David J Williams

doi:10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO;2-P

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

Angew Chem Int Ed Engl. 1998 Feb 16;37(3):333-337. doi: 10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO;2-P.

Affiliations

¹ School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT (UK).
² Dipartimento di Chimica "G. Ciamician", Università di Bologna, Via Selmi 2, I-40126 Bologna (Italy), Fax: Int. code+(39) 51 259-456.
³ Chemical Crystallography Laboratory, Department of Chemistry, Imperial College, South Kensington, London SW7 2AY (UK), Fax: Int. code+(44) 171 594-5804.

PMID: 29711270
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO;2-P

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.

Keywords: Catenanes; Charge transfer complexes; Molecular devices; Redox switching; Self-assembly; Supramolecular chemistry.