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Assembly of [2]Rotaxanes in Water
Author(s) -
Aeschi Yves,
DrayssOrth Sylvie,
Valášek Michal,
Raps Felix,
Häussinger Daniel,
Mayor Marcel
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700640
Subject(s) - chemistry , rotaxane , alkyne , cyclophane , ethylene glycol , azide , click chemistry , propargyl , molecular recognition , titration , polymer chemistry , naphthalene , inclusion compound , catenane , supramolecular chemistry , stereochemistry , combinatorial chemistry , organic chemistry , cyclodextrin , molecule , catalysis
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.