Calixarene-based Anion Receptors

Matthews, Susan E.; Beer, Paul D.

doi:10.1080/10610270500127089

Cited by 209 publications

(109 citation statements)

References 140 publications

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“…[11][12][13] We have undertaken a research programme with the objective of exploiting the unique topological cavities of rotaxanes and catenanes in anion host-guest chemistry. [10][11][12][14][15][16] We have previously reported the synthesis of heteroditopic calix [4]arene receptors which exhibit unprecedented cooperative and ion-pair binding behaviour. [17,18] Through suitable modification of this heteroditopic receptor design, together with exploitation of a strategic anion templation methodology, calix [4]arene functionalised [2]catenane anion receptors were assembled.…”

Section: Introductionmentioning

confidence: 99%

“…[10][11][12][14][15][16] We have previously reported the synthesis of heteroditopic calix [4]arene receptors which exhibit unprecedented cooperative and ion-pair binding behaviour. [17,18] Through suitable modification of this heteroditopic receptor design, together with exploitation of a strategic anion templation methodology, calix [4]arene functionalised [2]catenane anion receptors were assembled. [11,12] Herein we describe the preparation of the first calix [4]arene-based [2]rotaxane anion host systems, which consist of a calix [4]arene functionalised macrocycle wheel and pyridinium axle components, through adaptation of a new synthetic pathway that involves anion templation in combination with favourable p-p stacking interactions.…”

Section: Introductionmentioning

confidence: 99%

“…[17,18] Through suitable modification of this heteroditopic receptor design, together with exploitation of a strategic anion templation methodology, calix [4]arene functionalised [2]catenane anion receptors were assembled. [11,12] Herein we describe the preparation of the first calix [4]arene-based [2]rotaxane anion host systems, which consist of a calix [4]arene functionalised macrocycle wheel and pyridinium axle components, through adaptation of a new synthetic pathway that involves anion templation in combination with favourable p-p stacking interactions. [15] Anion binding investigations reveal the more preorganised rotaxane exhibits an impressive high affinity for chloride Abstract: The synthesis, structure and anion binding properties of the first calix [4]arene-based [2]rotaxane anion host systems are described.…”

Section: Introductionmentioning

confidence: 99%

“…[3] Calixarenes are attractive molecular structural frameworks renowned for their versatility and ease of functionalisation at both the narrow lower, and wide upper rim. [4,5] As a result a multitude of calixarene derivatives have been utilised as cation, [6] anion [4,7] and ion-pair receptors. [8] They have also recently begun to be incorporated into interlocked structures including rotaxanes [9,10] and catenanes.…”

Section: Introductionmentioning

confidence: 99%

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Calix[4]arene‐Based Rotaxane Host Systems for Anion Recognition

McConnell

Serpell

Thompson

et al. 2010

Chemistry A European J

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The synthesis, structure and anion binding properties of the first calix[4]arene-based [2]rotaxane anion host systems are described. Rotaxanes 9.Cl and 12.Cl, consisting of a calix[4]arene functionalised macrocycle wheel and different pyridinium axle components, are prepared via adaption of an anion templated synthetic strategy to investigate the effect of preorganisation of the interlocked host's binding cavity on anion binding. Rotaxane 12.Cl contains a conformationally flexible pyridinium axle, whereas rotaxane 9.Cl incorporates a more preorganised pyridinium axle component. The X-ray crystal structure of 9.Cl and solution phase (1)H NMR spectroscopy demonstrate the successful interlocking of the calix[4]arene macrocycle and pyridinium axle components in the rotaxane structures. Following removal of the chloride anion template, anion binding studies on the resulting rotaxanes 9.PF(6) and 12.PF(6) reveal the importance of preorganisation of the host binding cavity on anion binding. The more preorganised rotaxane 9.PF(6) is the superior anion host system. The interlocked host cavity is selective for chloride in 1:1 CDCl(3)/CD(3)OD and remains selective for chloride and bromide in 10 % aqueous media over the more basic oxoanions. Rotaxane 12.PF(6) with a relatively conformationally flexible binding cavity is a less effective and discriminating anion host system although the rotaxane still binds halide anions in preference to oxoanions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Calix[4]arene‐Based Rotaxane Host Systems for Anion Recognition

McConnell

Serpell

Thompson

et al. 2010

Chemistry A European J

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“…In another study by Yilmaz et al, 96 the Mannich base 27 was synthesized by the reaction of calix [4]arene with a cyclic secondary amine (1,4-dioxa-8-azaspiro- [4,5]decane) and formaldehyde. Then compound 27 was treated with dibromoxylene to give calix [4]arene-based copolymer 28 ( Figure 19).…”

Section: Investigated the Extraction Abilities Of P-tert-butylcalix[nmentioning

confidence: 99%

Calixarene-Based Receptors for Molecular Recognition

YILMAZ

2013

Turk J Chem

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Supramolecular Chemistry

Cragg

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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Supramolecular chemistry has its origins in the supermolecule, a term used by Nobel Laureate Jean‐Marie Lehn from the early 1970s when referring to a well‐defined chemical species comprised of several components. The realization that supermolecules could in turn form larger molecular assemblies led to the shift in emphasis from super‐ to supramolecular in the literature to more accurately describe the complexity of systems involved. Supramolecular chemistry has since advanced to include complexes between molecules with complementary binding sites (molecular recognition), multicomponent complexes (supramolecular assemblies), the programmed interactions between large molecular assemblies (molecular tectonics), and even the directed assembly of three‐dimensional solids (crystal engineering and metal–organic frameworks).This article sets out the concepts and aims of supramolecular chemistry, illustrates some of the early development in the field, considers the synthesis and structures of individual supramolecular synthons as well as supramolecular assemblies, and concludes with an assessment of current and anticipated applications in materials science, medicine, the interface with biology, molecular computing, nanomaterials, and nanomachines.

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Calixarene-based Anion Receptors

Cited by 209 publications

References 140 publications

Calix[4]arene‐Based Rotaxane Host Systems for Anion Recognition

Calix[4]arene‐Based Rotaxane Host Systems for Anion Recognition

Calixarene-Based Receptors for Molecular Recognition

Supramolecular Chemistry

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