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Assembly of [2]Rotaxanes in Water
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4103374
Author(s) Aeschi, Yves; Drayss-Orth, Sylvie; Valasek, Michal; Raps, Felix; Haussinger, Daniel; Mayor, Marcel
Author(s) at UniBasel Mayor, Marcel
Drayss-Orth, Sylvie Carolin
Raps, Felix Calvin
Aeschi, Yves
Häussinger, Daniel
Year 2017
Title Assembly of [2]Rotaxanes in Water
Journal European Journal of Organic Chemistry
Volume 2017
Number 28
Pages / Article-Number 4091-4103
Keywords Rotaxanes; Click chemistry; Cyclophanes; Host-guest systems
Abstract Two [2]rotaxanes have been assembled in water from modular subunits through Cu-I-catalyzed azide-alkyne click chemistry. For this purpose, 2,6-disubstituted naphthalene axles with solubilizing oligo(ethylene glycol) (OEG) chains (n = 1-5) and propargyl terminal groups were synthesized and examined for their propensity to form inclusion complexes with a dicationic Diederich-type cyclophane host. The dependence of pseudorotaxane formation on the linkers between the naphthalene core and OEG chains, and in the case of ester linkers on different spacer lengths, was analyzed by titration experiments. In addition, the inclusion complexes of two [2]rotaxanes were trapped by using a water-soluble azide-functionalized stopper. Repetitive chromatography finally enabled the isolation of both mechanically interlocked [2]rotaxanes.
Publisher Wiley
ISSN/ISBN 1434-193X ; 1099-0690
edoc-URL https://edoc.unibas.ch/63278/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/ejoc.201700640
ISI-Number 000407038200005
Document type (ISI) Article
 
   

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