Issue 9, 2017

Impact of mechanical bonding on the redox-switching of tetrathiafulvalene in crown ether–ammonium [2]rotaxanes

Abstract

Switchable crown ether–ammonium [2]rotaxanes with a redox-active tetrathiafulvalene (TTF) unit implemented in their wheels were synthesised and fully characterised. Reversible operation in two modes is possible, in which the [2]rotaxane's axle is either charged or neutral. Cyclic voltammetry experiments reveal the effects of mechanical bonding on the electrochemical properties of TTF and show the [2]rotaxanes to perform a distinct function in both modes. In the charged mode, redox-switching is dominated by strong electrostatic repulsion in the [2]rotaxane which subsequently leads to a macrocycle translation along the axle. In the non-charged mode, a selective energetic stabilisation of TTF radical cations is observed, which can be attributed to an interplay of weak electrostatic interactions between wheel and axle.

Graphical abstract: Impact of mechanical bonding on the redox-switching of tetrathiafulvalene in crown ether–ammonium [2]rotaxanes

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Jūn. 2017
Accepted
07 Jūl. 2017
First published
10 Jūl. 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 6300-6306

Impact of mechanical bonding on the redox-switching of tetrathiafulvalene in crown ether–ammonium [2]rotaxanes

H. V. Schröder, S. Sobottka, M. Nößler, H. Hupatz, M. Gaedke, B. Sarkar and C. A. Schalley, Chem. Sci., 2017, 8, 6300 DOI: 10.1039/C7SC02694C

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