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dc.contributor.authorGaedke, Marius
dc.contributor.authorWitte, Felix
dc.contributor.authorAnhäuser, Jana
dc.contributor.authorHupatz, Henrik
dc.contributor.authorSchröder, Hendrik V.
dc.contributor.authorValkonen, Arto
dc.contributor.authorRissanen, Kari
dc.contributor.authorLützen, Arne
dc.contributor.authorPaulus, Beate
dc.contributor.authorSchalley, Christoph A.
dc.date.accessioned2020-01-03T08:37:28Z
dc.date.available2020-01-03T08:37:28Z
dc.date.issued2019
dc.identifier.citationGaedke, 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. <i>Chemical Science</i>, <i>10</i>(43), 10003-10009. <a href="https://doi.org/10.1039/C9SC03694F" target="_blank">https://doi.org/10.1039/C9SC03694F</a>
dc.identifier.otherCONVID_33932639
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/67080
dc.description.abstractA 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.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofseriesChemical Science
dc.rightsCC BY-NC 3.0
dc.titleChiroptical inversion of a planar chiral redox-switchable rotaxane
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202001031014
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange10003-10009
dc.relation.issn2041-6520
dc.relation.numberinseries43
dc.relation.volume10
dc.type.versionpublishedVersion
dc.rights.copyright© The Royal Society of Chemistry 2019
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber309399
dc.relation.grantnumber314343
dc.subject.ysomakromolekyylit
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p139
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/3.0/
dc.relation.doi10.1039/C9SC03694F
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramTutkijaliikkuvuusrahoitus, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramResearcher mobility Funding, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundinginformationWe thank the Deutsche Forschungsgemeinschaft (CRC 765) and Academy of Finland (KR proj. no. 309399, AV proj. no. 314343) for funding. We are grateful to the Alexander von Humboldt-Foundation for support of KR (AvH research award). JA thanks the Studienstiftung des deutschen Volkes for a doctoral scholarship.


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