Journal ArticleDOI
The cooperative effect in ion-pair recognition by a ditopic hemicryptophane host.
TLDR
The heteroditopic hemicryptophane 1, which bears a tripodal anion binding site and a cation recognition site in the molecular cavity, proved to be an efficient ion-pair receptor.Abstract:
The heteroditopic hemicryptophane 1, which bears a tripodal anion binding site and a cation recognition site in the molecular cavity, proved to be an efficient ion-pair receptor. The hemicryptophane host binds anions selectively depending on shape and hydrogen-bond-accepting ability. It forms an inclusion complex with the Me(4)N(+) ion, which can simultaneously bind anionic species to provide anion@[1⋅Me(4)N(+)] complexes. The increased affinity of [1⋅Me(4)N(+)] for anionic species is attributed to a strong cooperative effect that arises from the properly positioned binding sites in the hemicryptophane cavity, thus allowing the formation of the contact ion pair. Density functional theory calculations were performed to analyze the Coulomb interactions of the ion pairs, which compete with the ion-dipole ones, that originate in the ion-hemicryptophane contacts.read more
Citations
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Journal ArticleDOI
Macrocycles as Ion Pair Receptors
Qing He,Qing He,Gabriela I. Vargas-Zúñiga,Seung Hyun Kim,Sung Kuk Kim,Jonathan L. Sessler,Jonathan L. Sessler +6 more
TL;DR: The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors and specifically focuses on the relationship between structure and ion pair recognition, as well as applications of ions pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction.
Journal ArticleDOI
Emergence of Hemicryptophanes: From Synthesis to Applications for Recognition, Molecular Machines, and Supramolecular Catalysis
TL;DR: Hemmicryptophanes are revealed to be inherently chiral ditopic host compounds, able to encapsulate various guests, including charged and neutral species, and enter the field of stimuli-responsive supramolecular systems exhibiting controlled functions.
Journal ArticleDOI
Cooperativity and Complexity in the Binding of Anions and Cations to a Tetratopic Ion-Pair Host
TL;DR: The insight into the complexity of cooperative interactions revealed in this study of the tetratopic ion-pair host 1 can be used to design better cooperative supramolecular systems for information transfer and catalysis.
Journal ArticleDOI
Combined cation-π and anion-π interactions for zwitterion recognition.
TL;DR: Brothers and enemies: Anion-π and cation-π interactions act in a synergistic way when gathered in the molecular cavity of a hemicryptophane host, affording an efficient contribution in zwitterion recognition.
Journal ArticleDOI
Oxidation of cycloalkanes by H2O2 using a copper–hemicryptophane complex as a catalyst
TL;DR: Efficient alkane C-H bond oxidation was achieved using a newly designed Cu(II)-hemicryptophane complex that allows discriminating cyclohexane from cyclooctane or adamantane in competitive experiments.
References
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TL;DR: Using NMR spectroscopy and X-ray crystallography, this work finds that 2 is the first example of a ditopic salt-receptor that binds a contact ion-pair in solution more strongly than either of the free ions.