10.1021/cg500420u.s002
Nicholas G. White
Nicholas G.
White
Christopher J. Serpell
Christopher J.
Serpell
Paul D. Beer
Paul D.
Beer
Structural Study of Triazole and Amide Containing
Anion-Templated Pseudorotaxanes
American Chemical Society
2014
macrocycle
template pseudorotaxane formation
oxoanions nitrate
benzoate display
steric demands
Structural Study
oxoanion templated pseudorotaxanes
halide anions
component
solution 1 H NMR experiments
HSO
interpenetrated assemblies
pyridinium
2014-07-02 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Structural_Study_of_Triazole_and_Amide_Containing_Anion_Templated_Pseudorotaxanes/2278336
The
ability of a range of halides and oxoanions to template pseudorotaxane
formation between an isophthalamide containing macrocycle and either
bis-triazole pyridinium or bis-amide pyridinium threading components
was investigated. Solution <sup>1</sup>H NMR experiments reveal that
all of the studied anions (Cl<sup>–</sup>, Br<sup>–</sup>, I<sup>–</sup>, NO<sub>3</sub><sup>–</sup>, HSO<sub>4</sub><sup>–</sup>, OAc<sup>–</sup>, and BzO<sup>–</sup>) can template interpenetrated assemblies. The solid-state structures
of nine of the pseudorotaxanes were determined by single crystal X-ray
structural analysis. In the solid state, the oxoanions nitrate, acetate
and benzoate display much stronger hydrogen bonding with the macrocycle
and threading components than the halide anions. Conversely, aromatic
donor–acceptor contacts between the macrocycle and thread are
significantly longer in the oxoanion templated pseudorotaxanes, presumably
due to the greater steric demands of these larger templates.