From Heteroditopic to Multitopic Receptors for Ion‐Pair Recognition: Advances in Receptor Design and Applications

McConnell, Anna J.; Docker, Andrew; Beer, Paul D.

doi:10.1002/cplu.202000484

Cited by 57 publications

(50 citation statements)

References 96 publications

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“…A solution to this problem may lie in the use of ion pair receptors able to interact with cations and anions simultaneously [ 38 , 39 , 40 , 41 , 42 ]. Surprisingly, the literature offers few reports of tripodal, TREN-based ion pair receptors and to the best of our knowledge this is limited to the tripodal amide designed by Beer and coworkers [ 43 ].…”

Section: Introductionmentioning

confidence: 99%

Tripodal, Squaramide-Based Ion Pair Receptor for Effective Extraction of Sulfate Salt

2021

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Combining three features—the high affinity of squaramides toward anions, cooperation in ion pair binding and preorganization of the binding domains in the tripodal platform—led to the effective receptor 2. The lack of at least one of these key elements in the structures of reference receptors 3 and 4 caused a lower affinity towards ion pairs. Receptor 2 was found to form an intramolecular network in wet chloroform, which changed into inorganic–organic associates after contact with ions and allowed salts to be extracted from an aqueous to an organic phase. The disparity in the binding mode of 2 with sulfates and with other monovalent anions led to the selective extraction of extremely hydrated sulfate anions in the presence of more lipophilic salts, thus overcoming the Hofmeister series.

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Section: Introductionmentioning

confidence: 99%

Tripodal, Squaramide-Based Ion Pair Receptor for Effective Extraction of Sulfate Salt

2021

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“…The reaction mixtures were subjected to an NH 4 OH/EDTA (aq) work up procedure after which the respective crude mixture was purified by iterative trituration protocols (see Supporting Information) using diethyl ether and methanol to afford the receptors 1 • XB, 1 • HB, 2 • XB and 2 • HB in yields in the range of 47-69 %. All of the heteroditopic receptors were characterised by 1 H and 13 C NMR and high resolution mass spectrometry.…”

Section: Design and Synthesis Of Xb And Hb Heteroditopic Receptor Functionalised Silica Materialsmentioning

confidence: 99%

Halogen Bonding Heteroditopic Materials for Cooperative Sodium Iodide Binding and Extraction

Docker

Stevens

Beer

2021

Chemistry A European J

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A series of novel heteroditopic halogen bonding (XB) receptor functionalised silica based materials, containing mono-and bis-iodotriazole benzo-15-crown-5 groups are investigated for the cooperative binding and extraction of sodium halide ion-pair species from aqueous solution. Characterisation of the XB materials by CHN elemental analysis, 13 C CP/MAS NMR and ATR-FTIR spectroscopies confirms and quantifies the successful incorporation of the ion-pair receptor frameworks to the silica material. ICP-MS solid-liquid extraction studies demonstrate the bidentate XB functionalised material is capable of NaI extraction from water. Importantly, cooperative XB-mediated sodium halide ion-pair binding is determined to be crucial to the material's extraction capabilities, impressively demonstrating a two-fold enhancement in sodium iodide extraction efficiency relative to a heteroditopic hydrogen bonding receptor functionalised silica material analogue.

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“…However, in some processes, the presence of strongly coordinating cations may hamper the action of monotopic anion receptors, as competitive ion pairing occurs [ 18 , 19 ]. A solution to this problem may lie in designing heteroditopic ion pair receptors which, possessing both cation and anion binding domains, are capable of binding ion pairs simultaneously [ 20 , 21 , 22 , 23 ]. Apart from the selection of binding sites, their proper arrangement on the molecular platform is important from the point of view of cooperativity in ion binding, which translates directly into the effectiveness of the receptors [ 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions

Jagleniec¹,

Walczak²,

Romański³

2021

IJMS

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A 4-nitro-L-phenylalanine scaffold was used to construct effective ion pair receptors capable of binding anions in an enhanced manner with the assistance of alkali metal cations. A benzocrown ether was linked to a receptor platform via the amide function so as to support the squaramide function in anion binding and to allow all three NHs to act simultaneously. The binding properties of the receptors were determined using UV-vis, 1H NMR, 2D NMR, and DOSY spectroscopy in MeCN and in the solid state by X-ray measurements. Ion pair receptor 2 was found to interact with the most strongly with salts, and the removal of its key structural elements was shown to hinder the receptor action. The amide proton was recognized to switch from having involvement in an intramolecular hydrogen bond to interacting with anions upon complexation. Apart from carboxylates, which promote deprotonation, and other monovalent salts creating 1:1 complexes with the receptor, more complex equilibria were established upon the complexation of 2 with sulfates. Receptor 2 was shown to be capable of the extraction of ion pairs from the aqueous to organic phase and of the cation-enhanced transport chloride and sulfate anions across a bulk chloroform membrane. These features may open the door for its use in regulating ion concertation under interfacial conditions and acting as a potential drug to treat channelopathies.

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From Heteroditopic to Multitopic Receptors for Ion‐Pair Recognition: Advances in Receptor Design and Applications

Cited by 57 publications

References 96 publications

Tripodal, Squaramide-Based Ion Pair Receptor for Effective Extraction of Sulfate Salt

Tripodal, Squaramide-Based Ion Pair Receptor for Effective Extraction of Sulfate Salt

Halogen Bonding Heteroditopic Materials for Cooperative Sodium Iodide Binding and Extraction

Utilizing an Amino Acid Scaffold to Construct Heteroditopic Receptors Capable of Interacting with Salts under Interfacial Conditions

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