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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Clipping and stoppering anion templated synthesis of a [2]rotaxane host system
Yitong Li1, Kathleen M Mullen, João Sardinha
1Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK OX1 3QR.
Abstract:
A new [2]rotaxane host system containing nitro-isophthalamide macrocycle and polyether functionalised pyridinium axle components is prepared via clipping and stoppering synthetic methodologies using chloride anion templation. After removing the chloride anion template, (1)H NMR titration experiments reveal the unique interlocked host cavity to be highly selective for binding chloride and bromide in preference to basic oxoanions in competitive aqueous solvent mixtures. The rotaxane host system proved to be a superior anion complexant in comparison to the individual macrocycle and axle components. The anion binding affinity of the novel rotaxane is also investigated via molecular dynamics simulations and in general the structural data obtained corroborates the experimental solution anion recognition behaviour.
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