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Template‐Directed Synthesis of a [2]Rotaxane by the Clipping under Thermodynamic Control of a Crown Ether Like Macrocycle Around a Dialkylammonium Ion
Author(s) -
Glink Peter T.,
Oliva Ana I.,
Stoddart J. Fraser,
White Andrew J. P.,
Williams David J.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010518)40:10<1870::aid-anie1870>3.0.co;2-z
Subject(s) - rotaxane , crown ether , chemistry , polymer chemistry , diamine , molecule , supramolecular chemistry , ether , materials science , ion , organic chemistry
A dumbbell‐shaped dialkylammonium ion (see scheme) templates the formation, about its NH 2 + center, of a crown ether like macrocycle under thermodynamic control from dialdehyde and diamine precursors. The imine‐containing [2]rotaxane that ensues was converted by reduction into a kinetically stable interlocked molecule, which has been characterized in the solid state by X‐ray crystallography in both free base and salt forms.