Anion Binding of Short, Flexible Aryl Triazole Oligomers

The flexible, electropositive cavity of linear 1,4-diaryl-1,2,3-triazole oligomers provides a suitable host for complexation of various anions. The binding affinities for various combinations of oligomer and anion were determined by 1H NMR titrations. Effective ionic radius is found to be a primary...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-12, Vol.74 (23), p.8924-8934
Main Authors: Juwarker, Hemraj, Lenhardt, Jeremy M, Castillo, José C, Zhao, Emily, Krishnamurthy, Sibi, Jamiolkowski, Ryan M, Kim, Ki-Hyon, Craig, Stephen L
Format: Article
Language:English
Subjects:
Anions - chemistry
Binding Sites
Chemistry
Coordination compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Inorganic chemistry and origins of life
Macrocyclic Compounds
Magnetic Resonance Spectroscopy
Molecular Conformation
Organic chemistry
Polymers - chemistry
Preparations and properties
Solvents
Triazoles - chemistry
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Summary:The flexible, electropositive cavity of linear 1,4-diaryl-1,2,3-triazole oligomers provides a suitable host for complexation of various anions. The binding affinities for various combinations of oligomer and anion were determined by 1H NMR titrations. Effective ionic radius is found to be a primary determinant of the relative binding interactions of various guests, with small but measurable deviations in the case of nonspherical anions. Solvent effects are significant, and the strength of the binding interaction is found to depend directly on the donor ability of the solvent. A picture emerges in which anion binding can be effectively interpreted in terms of a competition between two solvation spheres: one provided by the solvent and a second dominated by a folded cavity lined with electropositive 1,2,3-triazole CH protons. Implications for rigid macrocycles and other multivalent hosts are discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901966f