Abstract
AbstractThe supramolecular interaction between 1,2‐bis(pyridinio)ethane axles and 24‐membered crown ether wheels provides a template for the formation of interpenetrated [2]pseudorotaxanes. The preformed [2]pseudorotaxanes can then be kinetically trapped to produce permanently interlocked [2]rotaxanes by stoppering with bulky groups that prevent the unthreading of the resulting dumbbell from the wheel. Six [2]rotaxanes were created using 24‐crown‐8 (24C8), dibenzo‐24‐crown‐8 (DB24C8) and dinaphtho‐24‐crown‐8 (DN24C8) as the wheel and two methods of stoppering; alkylation of a terminal pyridine with tert‐butylbenzyl groups and esterification of a terminal benzyl alcohol with p‐(tert‐butyl)benzoate groups. The [2]rotaxanes were characterized by 1H NMR spectroscopy, electro‐spray mass spectrometry and X‐ray crystallography.
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