Halogen bonding assisted selective removal of bromide

Chakraborty, Sourav; Dutta, Ranjan; Ghosh, Pradyut

doi:10.1039/c5cc05495h

Cited by 40 publications

(43 citation statements)

References 48 publications

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“…[32] Thea ffinity for ac ertain binding partner can be significantly increased by switching from bidentate complexation modes to multiple interaction points adjusted in ac oncerted manner.A lthough the design and synthesis of multidentate XB donors is rather challenging due to the strict linearity of the interaction, it also offers the advantage of creating more rigid and ordered structures with an improved selectivity. [25,26] This general design strategy was successfully used in different studies by implementing pyridinium (3), [33] imidazolium (4, 5), [34,35] or triazolium (6) [35] moieties to build at ridentate bowl-shaped cavity.T hese structures enabled anion binding in stable 1:1( 3, 5,a nd 6)o r1:3 (4)c omplexes through charge-assisted HB/XB interactions ( Figure 3).…”

Section: Mono- Bi- and Tridentate Cationic Receptorsmentioning

confidence: 99%

Halogen Bonding in Solution: Anion Recognition, Templated Self‐Assembly, and Organocatalysis

2018

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The halogen bond is a supramolecular interaction between a Lewis-acidic region of a covalently bound halogen and a Lewis base. It has been studied widely in silico and experimentally in the solid state; however, solution-phase applications have attracted enormous interest in the last few years. This Minireview highlights selected recent developments in halogen bond interactions in solution, with a focus on the use of receptors based on halogen bonds in anion recognition and sensing, anion-templated self-assembly, as well as in organocatalysis.

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Section: Mono- Bi- and Tridentate Cationic Receptorsmentioning

confidence: 99%

Halogen Bonding in Solution: Anion Recognition, Templated Self‐Assembly, and Organocatalysis

2018

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“…[28] Chudzinski et al [29] obtained quantitativee stimates of the contribution of halogen bonding to the binding of anions to bipodal receptors, along with notingapreferencef or halides over oxoanions. [32] Our own group has engaged in severalr ecent studies in this arena,w here our quantum calculations have compared halogen with hydrogen-bonded receptors.R eplacemento ft he Hbondingp rotons of bis-triazole-pyridine by halogen atoms [33] demonstratedt hat Is ubstitution yields the greatest binding enhancementw ith various halides. Halogen bonding exertss electivity for bromide over chloride, or othera nions in as et of tripodalr eceptors.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Halide Receptors Based on Chalcogen, Pnicogen, and Tetrel Bonds

Scheiner

2016

Chemistry A European J

102

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The interactions of halides with a number of bipodal receptors were examined by quantum chemical methods. The receptors were based on a dithieno thiophene framework in which two S atoms can engage in a pair of chalcogen bonds with a halide. These two S atoms were replaced by P and As atoms to compare chalcogen with pnicogen bonding, and by Ge which engages in tetrel bonds with the receptor. Zero, one, and two O atoms were added to the thiophene S atom which is not directly involved in the interaction with the halides. Fluoride bound the most strongly, followed by Cl , Br , and I , respectively. Replacing S by the pnicogen bonds of P strengthened the binding, as did moving down to As in the third row of the periodic table. A further large increment is associated with the switch to the tetrel bonds of Ge. Even though the thiophene S atom is remote from the binding site, each additional O atom added to it raises the binding energy, which can be quite large, as much as 63 kcal mol for the Ge⋅⋅⋅F interaction. The receptors have a pronounced selectivity for F over the other halides, as high as 27 orders of magnitude. The data suggest that incorporation of tetrel atoms may lead to new and more powerful halide receptors.

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“…[1][2][3][4][5][6] Regarding the latter,w ea nd others have demonstrated that XB hosts often display superior anion affinities and contrasting selectivities in comparison to HB host analogues. [7][8][9][10][11] However,e xamples of XB host systems that function in competitive aqueous media remain extremely rare due in part to the challenging syntheses of such systems. [12,13] This is especially the case with elaborate XB mechanically interlocked molecules (MIMs), which due to their unique topological three-dimensional and highly preorganized cavities are capable of aqueous anion recognition.…”

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confidence: 99%

A Potent Halogen‐Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis

et al. 2019

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The covalent attachment of electron deficient perfluoroaryl substituents to ab is-iodotriazole pyridinium group produces ar emarkably potent halogen bonding donor motif for anion recognition in aqueous media. Sucham otif also establishes halogen bonding anion templation as ahighly efficient method for constructing am echanically interlocked molecule in unprecedented near quantitative yield. The resulting bis-perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by af actor of at least three orders of magnitude greater in comparison to ah ydrogen bonding rotaxane host analogue.T hese observations further champion and advance halogen bonding as apowerfultool for recognizing anions in aqueous media.

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Halogen bonding assisted selective removal of bromide

Cited by 40 publications

References 48 publications

Halogen Bonding in Solution: Anion Recognition, Templated Self‐Assembly, and Organocatalysis

Halogen Bonding in Solution: Anion Recognition, Templated Self‐Assembly, and Organocatalysis

Highly Selective Halide Receptors Based on Chalcogen, Pnicogen, and Tetrel Bonds

A Potent Halogen‐Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis

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