Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 3, Pages 479-485Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403380
Keywords
Supramolecular chemistry; Inclusion complexes; Rotaxanes; Pillar[5]arenes; Amides
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Funding
- Swiss National Science Foundation [200020-140298]
- International Center for Frontier Research in Chemistry (icFRC)
- LabEx Chimie des Systemes Complexes
- FUNDAYACUCHO
- University of Strasbourg [IdEx 2013]
- Swiss National Science Foundation (SNF) [200020_140298] Funding Source: Swiss National Science Foundation (SNF)
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Pillar[5]arene-based [2]rotaxanes have been prepared from the reactions of diacyl chloride reagents with various amine stoppers. The yields of the [2]rotaxanes are sensitive to the reaction conditions (solvent and stoichiometry) as well as to structural and electronic factors. In particular, the nature of the starting amine reagent has a dramatic influence on the yields of [2]rotaxanes; thus, the reaction outcome is not simply related to the binding constant of the diacyl chloride reagent with the pillar[5]arene. Indeed, the differences in the yields must be related to the different affinities for the various monoacylated intermediates. The yields of the [2]rotaxanes are also influenced by several structural factors such as the chain length of the diacyl chloride reagent and the size of the peripheral substituents of the pillar[5]arene building block. Finally, the preparation of [2]rotaxanes from alkyldiamine reagents and acyl chloride stoppers has also been investigated.
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