Lithium-selective phosphine oxide-based ditopic receptors show enhanced halide binding upon alkali metal ion coordination

Gavette, Jesse V.; Lara, Juven; Reling, Linda L.; Haley, Michael M.; Johnson, Darren W.

doi:10.1039/c2sc21501b

Cited by 21 publications

(15 citation statements)

References 37 publications

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“…However, lithium selective salt recognition could not be achieved. In fact, more broadly, receptors capable of recognizing the Li + cation or lithium ion pairs are rare. Those capable of extracting simple lithium salts are all but unknown.…”

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confidence: 99%

Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite

Zhang

Brewster

et al. 2016

J. Am. Chem. Soc.

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The hemispherand-strapped calix[4]pyrrole (1) acts as an ion pair receptor that exhibits selectivity for lithium salts. In organic media (CD2Cl2 and CD3OD, v/v, 9:1), receptor 1 binds LiCl with high preference relative to NaCl, KCl, and RbCl. DFT calculations provided support for the observed selectivity. Single crystal structures of five different lithium ion-pair complexes of 1 were obtained. In the case of LiCl, a single bridging water molecule between the lithium cation and chloride anion was observed, while tight contact ion pairs were observed in the case of the LiBr, LiI, LiNO3, and LiNO2 salts. Receptor 1 proved effective as an extractant for LiNO2 under both model solid-liquid and liquid-liquid extraction conditions.

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confidence: 99%

Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite

Zhang

Brewster

et al. 2016

J. Am. Chem. Soc.

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“…This indicates that prebound metal cations can enhance the complexation of anions by these ditopic receptors. Recently, the Johnson and Haley groups also revealed a similar phenomenon with a phosphine oxide based ditopic receptor …”

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confidence: 67%

Convergent Ditopic Receptors Enhance Anion Binding upon Alkali Metal Complexation for Catalyzing the Ritter Reaction

et al. 2019

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A supramolecular approach to catalyzing the Ritter reaction by utilizing enhanced anion-binding affinity in the presence of alkali metal cations was developed with ditopic hydrogen-bonded amide macrocycles. With prebound cations in the macrocycle, particularly Li + ion, their metal complexes exhibit greatly enhanced catalytic activities. The catalysis is switchable by removal or addition of the bound cation. The method described in this work may be generalized for use in other aniontriggered organic reactions involving heteroditopic receptors capable of ion pairing.

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“…Since these receptors benefit from synergistic effects between the co‐bound ions, such as electrostatic and allosteric interactions, they exhibit enhanced binding affinities. Additionally, the modification of the recognition sites allows for fine‐tuning the selectivity, thus, a plethora of receptors has been designed for efficient binding of alkali metal (MX) and tetraalkylammonium salts (R 4 NX) . As such, IP receptors have emerged as potential candidates for numerous applications, such as salt extraction, transmembrane transport, and catalysis …”

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confidence: 99%

Enhancement of Ion Pairing of Sr(II) and Ba(II) Salts by a Tritopic Ion‐Pair Receptor in Solution

et al. 2020

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Tritopic ion‐pair receptors can bind bivalent salts in solution; yet, these salts have a tendency to form ion‐pairs even in the absence of receptors. The extent to which such receptors can enhance ion pairing has however remained elusive. Here, we study ion pairing of M2+ (Ba2+, Sr2+) and X− (I−, ClO4−) in acetonitrile with and without a dichlorooxacalix[2]arene[2]triazine‐related receptor containing a pentaethylene‐glycol moiety. We find marked ion association already in receptor‐free solutions. When present, most of the MX+ ion‐pairs are bound to the receptor and the overall degree of ion association is enhanced due to coordinative, hydrogen‐bonding, and anion‐π interactions. The receptor shows higher selectivity for iodides but also stabilizes perchlorates, despite the latter are often considered as weakly coordinating anions. Our results show that ion‐pair binding is strongly correlated to ion pairing in these solutions, thereby highlighting the importance of taking ion association in organic solvents into account.

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Lithium-selective phosphine oxide-based ditopic receptors show enhanced halide binding upon alkali metal ion coordination

Cited by 21 publications

References 37 publications

Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite

Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite

Convergent Ditopic Receptors Enhance Anion Binding upon Alkali Metal Complexation for Catalyzing the Ritter Reaction

Enhancement of Ion Pairing of Sr(II) and Ba(II) Salts by a Tritopic Ion‐Pair Receptor in Solution

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