A novel receptor for dicarboxylic acid derivatives

Flack, Stephen S.; Chaumette, Jean-Louis; Kilburn, Jeremy D.; Langley, G. John; Webster, Michael

doi:10.1039/c39930000399

Cited by 33 publications

(16 citation statements)

References 9 publications

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“…In an early example, Kilburn and coworkers showed that compound 1.41 forms strong complexes with the mono-potassium salts of dicarboxylic acids and phenyl phosphonate, binding these guests as contact ion pairs (Figure 1.21). 54 A series of solid-liquid and liquid-liquid extraction experiments provided support for the suggestion that this ditopic receptor is able to effect the transfer…”

Section: Ion Pair Receptors That Contain Amide Groups For Anion Recogmentioning

confidence: 93%

“…99 Nucleobases 1.93 and 1.94 which combine to form a G-quartet (G 3) 4 and an A-quartet (A 1) 4 , respectively, recognize the Na + cation and the Cl -anion. The ion-filled DNA-base quartets are thought to stack so as to allow a direct interaction between the bound Na + cation and Cl -anion (Figure 1. 54). 4 and their proposed cooperative recognition of NaCl.…”

Section: Ion Pair Receptors Based On G-quartetsmentioning

confidence: 99%

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Calix[4]pyrrole-Based Ion Pair Receptors

2014

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Ion pair receptors, which are able to bind concurrently both a cation and an anion, often display higher selectivity and affinity for specific ion pairs than simple ion receptors capable of recognizing primarily either a cation or an anion. This enhancement in recognition function is attributable to direct or indirect cooperative interactions between cobound ions via electrostatic attractions between oppositely charged ions, as well as to positive allosteric effects. In addition, by virtue of binding the counterions of the targeted ion, ion pair receptors can minimize the solvation of the counterions, which can otherwise have a negative effect on the interactions between the receptors and the targeted ions. As a result of their more favorable interactions, ion pair receptors are attractive for use in applications, such as extraction and sensing, where control of the binding interactions is advantageous. In this Account, we illustrate this potential in the context of ion pair receptors based on the calix[4]pyrrole scaffold. Both simple ditopic ion pair receptors, containing sites for the recognition of a single anion and single cation, and so-called multitopic ion pair receptors will be discussed. The latter systems differ from conventional, so-called ditopic ion pair receptors in that they contain more than one binding site for a given targeted ion (e.g., a cation). This permits a level of selectivity and control over binding function not normally seen for simple ion or ion pair receptors containing one or two binding sites, respectively. Calix[4]pyrroles are macrocyclic compounds consisting of four pyrrole units linked via fully substituted sp 3 hybridized meso carbon atoms. They are effective receptors for Lewis basic anions (e.g., halides) in typical organic media and under certain conditions will recognize ion pairs containing charge diffuse cations, such as a small alkylammonium, imidazolium, or cesium cations. The calix[4]pyrrole framework is further attractive in that it is relatively easy to modify. In particular, functionalization of the β-pyrrolic carbon and meso-carbon atoms with simple crown ethers or calix[4]arene crown ethers can produce heteromultitopic ion pair receptors containing more than two cation binding sites. This allows the interactions between receptors and ions to be manipulated on a higher level than can be achieved using simple ion receptors or heteroditopic ion pair receptors and has made these systems attractive for use in ion transport, recognition, and extraction. Recent progress in developing calix[4]pyrroles as both multitopic and more conventional ion pair receptors is summarized in this Account. The emphasis will be on our own work.

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Section: Ion Pair Receptors That Contain Amide Groups For Anion Recogmentioning

confidence: 93%

Section: Ion Pair Receptors Based On G-quartetsmentioning

confidence: 99%

Calix[4]pyrrole-Based Ion Pair Receptors

2014

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“…Moreover, they offer the advantage of being preorganised and therefore capable of profiting from the thermodynamic macrobicyclic effect. It has been shown that lateral macrobicycles behave as very versatile receptors that can be used as platforms to obtain homo-and heterometallic dinuclear complexes with many different aims, that is, to induce processes of "push-pull" dimetallic substrate activation [22] and as receptors for organic molecules [23] or contact ion pairs. [24,25] However, to date the recognition of anions by this type of receptor has remained much less explored than cation recognition.…”

Section: Introductionmentioning

confidence: 99%

Protonated Macrobicyclic Hosts Containing Pyridine Head Units for Anion Recognition

Esteban‐Gómez

Platas‐Iglesias

Blas

et al. 2008

Chemistry A European J

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In this paper, we report two macrobicyclic receptors containing pyridine head units derived from 1,10-diaza-15-crown[5] (L1) or 4,13-diaza-18-crown[6] (L2) that can be protonated in MeCN and used for anion recognition. The interaction of these protonated lateral macrobicycles with different anions has been investigated by means of spectrophotometric titrations in MeCN. The association constants for the complexes of halide anions with the protonated macrobicycles follow the sequences Cl(-)>Br(-)>I(-)>F(-) (L1) and Cl(-)>F(-)>I(-)>Br(-) (L2), whereby an increase of more than two logarithmic units is observed from F(-) to Cl(-) for the binding constants of the receptor derived from L1. The association constants also indicate an important degree of selectivity of these macrobicyclic receptors for Cl(-) over Br(-) or I(-). The X-ray crystal structure analyses of the chloride and bromide complexes confirms the formation of the envisaged supramolecular complexes. Moreover, the binding constants indicate that these receptors present a high sulfate-to-nitrate binding selectivity. The stability trend observed for the recognition of halide anions by the macrobicycles presented herein as well as the sulfate-to-nitrate binding selectivity have been rationalised by means of DFT calculations at the B3LYP/LanL2DZ level. These studies indicate that the especially high binding selectivity for Cl(-) is the result of the optimum fit between the protonated macrobicyclic cavity and the size of the anion, whereas the sulfate-to-nitrate selectivity results from shape complementarity between the hydrogen-binding acceptor sites on sulfate and the hydrogen-bond donors of the macrobicycle.

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“…NMR studies performed in chloroform proved the interaction of different dicarboxylate anions and amino acids with this receptor [186]. The coordinatively unsaturated Cu 2+ centers can catch a pimelate anion as a bridging bis(monodentate) ligand as shown in the crystal structure presented in Figure 1.39 [187].…”

mentioning

confidence: 99%