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Chiroptical inversion of a planar chiral redox-switchable rotaxane

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Abstract

A tetrathiafulvalene (TTF)-containing crown ether macrocycle with Cs symmetry was designed to implement planar chirality into a redox-active [2]rotaxane. The directionality of the macrocycle atom sequence together with the non-symmetric axle renders the corresponding [2]rotaxane mechanically planar chiral. Enantiomeric separation of the [2]rotaxane was achieved by chiral HPLC. The electrochemical properties – caused by the reversible oxidation of the TTF – are similar to a non-chiral control. Reversible inversion of the main band in the ECD spectra for the individual enantiomers was observed after oxidation. Experimental evidence, conformational analysis and DFT calculations of the neutral and doubly oxidised species indicate that mainly electronic effects of the oxidation are responsible for the chiroptical switching. This is the first electrochemically switchable rotaxane with a reversible inversion of the main ECD band.

Graphical abstract: Chiroptical inversion of a planar chiral redox-switchable rotaxane

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Publication details

The article was received on 26 Jul 2019, accepted on 04 Sep 2019 and first published on 04 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03694F
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Chiroptical inversion of a planar chiral redox-switchable rotaxane

    M. Gaedke, F. Witte, J. Anhäuser, H. Hupatz, H. V. Schröder, A. Valkonen, K. Rissanen, A. Lützen, B. Paulus and C. A. Schalley, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03694F

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