Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

Cornes, Stuart; Davies, Charles H.; Blyghton, David; Sambrook, Mark R.; Beer, Paul D.

doi:10.1039/c4ob02547d

Cited by 23 publications

(10 citation statements)

References 31 publications

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“…This effect is most pronounced in spatially constrained binding sites, such as those of rotaxanes 25a and 25b, which differ only by the presence of an iodine atom on the axle's triazole unit (Figure 11). 50 In the protic solvent mixture CDCl 3 /CD 3 OD 1:1 v/v, HB rotaxane 25a binds H 2 PO 4 À selectively over the halides and acetate (K a (H 2 PO 4…”

Section: How Does Anion Binding By Xb and Hb Hosts Differ?mentioning

confidence: 99%

Sigma-Hole Interactions in Anion Recognition

Lim

Beer

2018

Chem

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350

292

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Sigma (s)-holes are electron-deficient regions that arise from the anisotropic distribution of electron density on the atom of group 14 (tetrels), 15 (pnictogens), 16 (chalcogens), and 17 (halogens) elements when covalently bonded to electron-withdrawing groups. Named after the donor atom's group, the s-hole interactions, halogen bonding, and chalcogen bonding with anionic species have found ground-breaking applications in anion supramolecular chemistry within the last decade. In this review, we feature key recent discoveries and advances across the whole range of s-hole interactions for anion recognition, from the familiar halogen bonding to the almost unknown pnictogen and tetrel bonding. In particular, the novel anion recognition properties and applications that result from the unique aspects of each s-hole interaction, together with detailed design considerations of anion-binding receptor motifs, are highlighted.

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Section: How Does Anion Binding By Xb and Hb Hosts Differ?mentioning

confidence: 99%

Sigma-Hole Interactions in Anion Recognition

Lim

Beer

2018

Chem

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350

292

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“…Benzohydrazide Twelve compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were synthesized according to the following method. Substituted benzohydrazide (1 mmol) was dissolved in dry ethanol (30 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Selective recognition and sensing of biologically important anions has attracted considerable attention in the field of supramolecular chemistry because of its important roles in medical, biological, chemical, and environmental systems [1][2][3][4][5][6][7][8][9][10]. For example, carboxylate ions are vital components of many human metabolic processes [11].…”

Section: Introductionmentioning

confidence: 99%

Double Properties of Novel Acylhydrazone Nanomaterials Based on a Conjugated System: Anion Binding Ability and Antibacterial Activity

Shang

Feng

et al. 2015

Applied Sciences

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A series of new compounds (1-12) containing 1,5-diaza-fluorenone, 1,10-phenanthroline-5,6-dione, ferrocene-1,1ʹ-dione, anthracene-9-carbaldehyde have been synthesized and optimized. The nanomaterials were also developed successfully. ) by theoretical investigation, UV-vis, and fluorescence experiments, and compound 6 displayed the strongest binding ability for AcO − ion among the synthesized compounds. Theoretical investigation analysis revealed that the intramolecular hydrogen bond existed in the structure of compound 6 and the roles of molecular frontier orbitals in molecular interplay. In addition, compound 6 showed wide antibacterial activity for colon bacillus, typhoid bacillus, and Pseudomonas aeruginosa, and inferior activity for hay bacillus and Staphylococcus aureus. This series of acylhydrazone nanomaterials showed double properties, anion binding ability, and antibacterial activity.

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“…Investigations of synthetic anion receptors have attracted considerable attention in the field of host-guest chemistry because of the important roles of anions in biomedicinal and chemical processes [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. The design of these receptors has focused on the ability to recognize and sense the biologically important anions selectively.…”

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental: The Synthetic and Anion-Binding Properties of Tripodal Salicylaldehyde Derivatives

Zhang

2016

Sensors

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A series of colorimetric anion probes 1–6 containing OH and NO2 groups were synthesized, and their recognition properties toward various anions were investigated by visual observation, ultraviolet–visible spectroscopy, fluorescence, 1H nuclear magnetic resonance titration spectra and theoretical investigation. Nanomaterials of three compounds 2–4 were prepared successfully. Four compounds 3–6 that contain electron-withdrawing substituents showed a high binding ability for AcO−. The host–guest complex formed through a 1:1 binding ratio, and color changes were detectable during the recognition process. Theoretical investigation analysis revealed that an intramolecular hydrogen bond existed in the structures of compounds and the roles of molecular frontier orbitals in molecular interplay. These studies suggested that this series of compounds could be used as colorimetric probes to detect of AcO−.

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Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

Cited by 23 publications

References 31 publications

Sigma-Hole Interactions in Anion Recognition

Sigma-Hole Interactions in Anion Recognition

Double Properties of Novel Acylhydrazone Nanomaterials Based on a Conjugated System: Anion Binding Ability and Antibacterial Activity

Theoretical and Experimental: The Synthetic and Anion-Binding Properties of Tripodal Salicylaldehyde Derivatives

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