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Rotaxanes Based on the 1,2‐Bis(pyridinio)ethane–24‐Crown‐8 Templating Motif
Author(s) -
Mercer Darren J.,
Vella Sarah J.,
Guertin Lianne,
Suhan Natalie D.,
Tiburcio Jorge,
Vukotic V. Nicholas,
Wisner James A.,
Loeb Stephen J.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001616
Subject(s) - chemistry , supramolecular chemistry , crown ether , alkylation , pyridine , crystallography , polymer chemistry , rotaxane , ether , stereochemistry , supramolecular chirality , medicinal chemistry , organic chemistry , crystal structure , catalysis , ion
The 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 1 H NMR spectroscopy, electro‐spray mass spectrometry and X‐ray crystallography.