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'Click' functionalised polymer resins: a new approach to the synthesis of surface attached bipyridinium and naphthalene diimide [2]rotaxanes.

Organic & biomolecular chemistry (2013-02-06)
Hannah Wilson, Sean Byrne, Nick Bampos, Kathleen M Mullen
ABSTRACT

Herein we describe the design and synthesis of a series of solid-tethered [2]rotaxanes utilising crown ether-naphthalene diimide or crown ether-bipyridinium host guest interactions. TentaGel polystyrene resins were initially modified in a two-stage procedure to azide functionalised beads before the target supramolecular architectures were attached using a copper catalysed "click" procedure. The final assembly was examined using IR spectroscopy and gel-phase (1)H High Resolution Magic Angle Spinning (HR MAS) NMR spectroscopy. The HR MAS technique enabled a direct comparison between the solid-tethered architectures and the synthesis and characterisation of analogous solution-based [2]rotaxanes to be made.