Removal of phosphate in presence of interfering sulphate and arsenate by a tripodal thiourea receptor by precipitation through crystallization in semi-aqueous medium

Ghosh, Tamal; Dutta, Ranjan; Maji, Siddhartha; Pal, Sarmistha; Ghosh, Pradyut

doi:10.1016/j.poly.2019.03.025

Cited by 5 publications

(8 citation statements)

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“…A significant number of organic receptors are known to bind with sulfate and phosphate anions by employing urea and ortho -bis-urea functional groups. , However, structural evidence of neutral organic receptors recognizing the arsenate anion (AsO 4 3– ) is limited with just two examples before this work. , …”

Section: Resultsmentioning

confidence: 99%

“…14,37 However, structural evidence of neutral organic receptors recognizing the arsenate anion (AsO 4 3− ) is limited with just two examples before this work. 30,31 Recognition of Sulfate, Phosphate, and Arsenate Anions in Solution State. Having examined the solid-state supramolecular complexes of the three oxyanions with newfound receptor 2, we decided to examine its ability to bind them in solution state with the same stoichiometry.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Effective strategies involve either macrocyclic or acyclic receptors with cleft or tripodal shapes that contain hydrogen-bonding functional groups, such as amides, ureas, and squaramides among others. − Several receptors that can efficiently and selectively recognize and extract sulfate and phosphate anions have been developed. − Synthetic receptors capable of binding either of the protonated forms of arsenate anions (HAsO 4 2– , H 2 AsO 4 – ) are limited. − Further, none exists with measured selective affinity for fully deprotonated AsO 4 3– , which is prevalent in oxidizing conditions and high-pH groundwater, , although a receptor is known to extract it from water . Furthermore, structural evidence for arsenate coordination through hydrogen bonding from charge-neutral organic receptors is still limited with one example for HAsO 4 2– and two examples for AsO 4 3– anions. ,, …”

Section: Introductionmentioning

confidence: 99%

“…30 Furthermore, structural evidence for arsenate coordination through hydrogen bonding from charge-neutral organic receptors is still limited with one example for HAsO 4 2− and two examples for AsO 4 3− anions. 22,30,31 Herein, we report the design and synthesis of a readily accessible bis-urea cleft receptor (2, Chart 1) and its anion recognition chemistry with sulfate, phosphate, and arsenate anions. Our cleft receptor is based on an N,N′-dimethyl-N,N′diphenylurea (1) scaffold.…”

Section: ■ Introductionmentioning

confidence: 99%

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Cleft Receptor for the Recognition and Extraction of Tetrahedral Oxyanions

Biswas

Ghorai

Paul

et al. 2023

Crystal Growth & Design

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We report the design and synthesis of a new cleft-shaped bis-urea receptor for the recognition of tetrahedral oxyanions from a foldameric N,N′-dimethyl-N,N′-diphenylurea scaffold. The receptor forms 3:1 host–guest complexes with sulfate, phosphate, and arsenate anions in the solid state by readily binding them through hydrogen bonding. 1H NMR analysis of binding events in a competitive medium (DMSO-d 6/H2O, 90:10) revealed that the receptor has a strong and selective affinity for arsenate (K a(3:1) = 2.41 (±0.79) × 108 M–3) in comparison with phosphate and no affinity for sulfate. The receptor extracts the three oxyanions from water into chlorinated organic solvents when the tetra-n-butyl ammonium ion is used as a cationic support. The receptor also crystallizes out the arsenate anion from water with faster kinetics in acetonitrile solution with a similar cationic support.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Cleft Receptor for the Recognition and Extraction of Tetrahedral Oxyanions

Biswas

Ghorai

Paul

et al. 2023

Crystal Growth & Design

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“…12 Tripodal thioureas were used to remove phosphates from aqueous media by precipitation in self-assembled capsules. 13 Other tripodal thioureas were used in the liquid−liquid extraction experiments. Up to 55 mol % of the dihydrogen phosphate was extracted into chloroform from its 10 mM aqueous solution, with part of the phosphate being extracted and converted to its monobasic form.…”

Section: ■ Introductionmentioning

confidence: 99%

An Insight into Anion Extraction by Amphiphiles: Hydrophobic Microenvironments as a Requirement for the Extractant Selectivity

Salvadori,

Onali,

Mathez

et al. 2023

ACS Omega

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Coupling of electron-deficient urea units with aliphatic chains gives rise to amphiphilic compounds that bind to phosphate and benzoate anions in the hydrogen bonding competitive solvent (DMSO) with K Ass = 6 580 M–1 and K Ass = 4 100 M–1, respectively. The anchoring of these receptor moieties to the dendritic support does not result in a loss of anion binding and enables new applications. Due to the formation of a microenvironment in the dendrimer, the high selectivity of the prepared compound toward benzoate is maintained even in the presence of aqueous media during extraction experiments. In the presence of binding sites at 5 mM concentration, the amount of benzoate corresponding to the full binding site occupancy is transferred into the chloroform phase from its 10 mM aqueous solution. A thorough investigation of the extraction behavior of the dendrimer reported here, supported by a series of molecular dynamics simulations, provides new insight into the fundamental principles of extraction of inorganic anions by amphiphiles.

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