Related Experiment Video
Updated: Jan 31, 2026

Electrochemically and Bioelectrochemically Induced Ammonium Recovery
Published on: January 22, 2015
Accordion-Like Motion in Electrochemically Switchable Crown Ether/Ammonium Oligorotaxanes
Hendrik V Schröder1, Felix Stein1, Jan M Wollschläger1
1Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195, Berlin, Germany.
Electrochemical oxidation of tetrathiafulvalene (TTF)-decorated rotaxanes causes wheel shuttling and length changes, like an accordion. This molecular motion is promising for developing new nanodevices and functional materials.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Nanotechnology
Background:
- Oligorotaxanes are molecular architectures with potential applications in nanodevices.
- Tetrathiafulvalene (TTF) units can undergo reversible redox reactions, enabling molecular switching.
- Controlling molecular motion is key to developing advanced functional materials.
Purpose of the Study:
- To investigate the electrochemical behavior of TTF-decorated oligorotaxanes.
- To understand how redox reactions influence the conformational changes and molecular motion within these systems.
- To explore the potential of these rotaxanes as components in nanodevices.
Main Methods:
- Electrochemical synthesis and characterization of TTF-decorated oligorotaxanes.
- Spectroscopic analysis to probe mixed-valence and radical-cation interactions.
- Structural analysis to observe changes in inter-wheel distances and conformational states.
- Comparison with control compounds lacking translational mobility.
Main Results:
- Reversible oxidation induced intramolecular interactions and shuttling of TTF-decorated crown ether wheels.
- Contraction and expansion of inter-wheel distances were observed, resembling accordion-like motion.
- These conformational changes were dependent on the redox state of the TTF units.
- Control experiments confirmed that translational motion is essential for this behavior.
Conclusions:
- Electrically switchable oligorotaxanes exhibit unique accordion-like molecular motion driven by redox-induced interactions.
- This controlled molecular movement opens possibilities for designing novel functional materials.
- The findings suggest potential applications in areas such as molecular motors and responsive nanodevices.
Related Concept Videos
Crown Ethers
What is an Electrochemical Gradient?
The chemical gradient relies on differences in the abundance of a substance on the outside versus the inside of a cell and flows from areas of high to low ion concentration. In contrast, the electrical gradient revolves around an...
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
Physical Properties of Ethers
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
Autoxidation of Ethers to Peroxides and Hydroperoxides

