A1 Journal article (refereed)
Chiroptical inversion of a planar chiral redox-switchable rotaxane (2019)


Gaedke, M., Witte, F., Anhäuser, J., Hupatz, H., Schröder, H. V., Valkonen, A., Rissanen, K., Lützen, A., Paulus, B., & Schalley, C. A. (2019). Chiroptical inversion of a planar chiral redox-switchable rotaxane. Chemical Science, 10(43), 10003-10009. https://doi.org/10.1039/C9SC03694F


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Publication details

All authors or editorsGaedke, Marius; Witte, Felix; Anhäuser, Jana; Hupatz, Henrik; Schröder, Hendrik V.; Valkonen, Arto; Rissanen, Kari; Lützen, Arne; Paulus, Beate; Schalley, Christoph A.

Journal or seriesChemical Science

ISSN2041-6520

eISSN2041-6539

Publication year2019

Volume10

Issue number43

Pages range10003-10009

PublisherRoyal Society of Chemistry

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/C9SC03694F

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/67080


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.


Keywordsmacromolecules


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Ministry reportingYes

Reporting Year2019

JUFO rating3


Last updated on 2024-08-01 at 18:54