Anion binding induced conformational changes exploited for recognition, sensing and pseudorotaxane disassembly

Abstract

Investigations to exploit the anion binding induced conformational changes displayed by a new class of acyclic receptor for anion recognition, fluorescence sensing and pseudorotaxane disassembly are described. A series of imidazolium-appended bis-amide-pyridine, pyridine N-oxide and pyridinium containing receptors are synthesised and their anion binding properties elucidated using ¹H NMR spectroscopy. Upon anion recognition, the receptors exhibit a substantial conformational change from an ‘open’ to a more ‘closed’ intramolecular geometry. The fluorescence anion sensing ability of a bis-pyrene-functionalised analogue is investigated, with anion-induced responses arising from excimer signalling mechanisms. A pseudorotaxane assembly formed between the pyridine N-oxide receptor acting as a threading component and an isophthalamide macrocycle is demonstrated to undergo disassembly resulting from the conformational behaviour exhibited by the thread upon chloride binding.