dc.contributor.author
Gaedke, Marius
dc.contributor.author
Hupatz, Henrik
dc.contributor.author
Witte, Felix
dc.contributor.author
Rupf, Susanne M.
dc.contributor.author
Douglas, Clara
dc.contributor.author
Schröder, Hendrik V.
dc.contributor.author
Fischer, Lukas
dc.contributor.author
Malischewski, Moritz
dc.contributor.author
Paulus, Beate
dc.contributor.author
Schalley, Christoph A.
dc.date.accessioned
2022-01-03T11:55:33Z
dc.date.available
2022-01-03T11:55:33Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/32946
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-32672
dc.description.abstract
From a library of five crown ether macrocycles with different ring sizes and redox-active moieties, such as tetrathiafulvalene (TTF) and naphthalene dimiide (NDI), directional heterocircuit[3]rotaxanes were constructed. Using an axle with two binding sites with different steric accessibility, the concept of integrative self-sorting was applied to program the sequence of functional units in heteropseudo[3]rotaxanes. Depending on binding strength and ring size of the smaller macrocycles, different heteropseudo[3]rotaxane selectivities and stabilities were determined by 2D NMR spectroscopy and tandem mass spectrometry. A heteropseudo[3]rotaxane with rotaxane-like behaviour was isolated chromatographically, displaying electrochemically “frustrated” properties. A robust synthetic procedure was developed allowing the synthesis of four new hetero[3]rotaxanes incorporating specific sequences of functional units. Sequence pseudoisomeric rotaxanes which have the naphthalene diimide subunit at two different positions show distinct electrochemical properties. DFT calculations suggest that this differences could arise from a folding of the structure, in which the redox-active moieties stack with a stopper unit. This study presents a blueprint for the construction of hetero[3]rotaxanes with sequential control of the functional units along the track of the axle and paves the way to extend the functionality of mechanically interlocked molecules.
en
dc.format.extent
11 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by/4.0/
dc.subject
construction
en
dc.subject
hetero[3]rotaxanes
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
Sequence-sorted redox-switchable hetero[3]rotaxanes
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.doi
10.1039/D1QO01553B
dcterms.bibliographicCitation.journaltitle
Organic Chemistry Frontiers
dcterms.bibliographicCitation.number
1
dcterms.bibliographicCitation.pagestart
64
dcterms.bibliographicCitation.pageend
74
dcterms.bibliographicCitation.volume
9
dcterms.bibliographicCitation.url
https://doi.org/10.1039/D1QO01553B
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
2052-4129
refubium.resourceType.provider
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