Triazole functionalized acyclic cucurbit[]uril-type receptors: host·guest recognition properties

We report the synthesis of three new triazole functionalized acyclic CB[ n ]-type receptors ( 2-4 ) by click chemistry. The compounds have good solubility in water (≥8 mM) and do not undergo strong self-association ( K s ≤ 903 M −1 ). We measured the binding constants of 2-4 toward guests 9-24 and c...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-06, Vol.17 (22), p.5561-5569
Main Authors: Xue, Weijian, Zavalij, Peter Y, Isaacs, Lyle
Format: Article
Language:English
Subjects:
Chemical synthesis
Click Chemistry
Crystal structure
Crystallography
Crystallography, X-Ray
Macrocyclic Compounds - chemical synthesis
Macrocyclic Compounds - chemistry
Models, Molecular
Molecular Conformation
NMR
Nuclear magnetic resonance
Organic chemistry
Receptor mechanisms
Receptors
Self-association
Solubility
Triazoles
Triazoles - chemistry
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Summary:We report the synthesis of three new triazole functionalized acyclic CB[ n ]-type receptors ( 2-4 ) by click chemistry. The compounds have good solubility in water (≥8 mM) and do not undergo strong self-association ( K s ≤ 903 M −1 ). We measured the binding constants of 2-4 toward guests 9-24 and compared the results to those obtained for the prototypical acyclic CB[ n ]-type receptor 1 . The X-ray crystal structure of 4 is also described. The synthesis, characterization, and molecular recognition properties of 2-4 toward organic ammonium ions in water is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00906j