Ditopic azathioether macrocycles as hosts for transition metal saltsElectronic supplementary information (ESI) available: full experimental details. See http://www.rsc.org/suppdata/cc/b1/b109486f/

Love, Jason B.; Vere, Joanna M.; Glenny, Mark W.; Blake, Alexander J.; Schröder, Martin

doi:10.1039/b109486f

Cited by 27 publications

(10 citation statements)

References 13 publications

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“…3 , 08C then RT; e) tert-butyl or n-butyl isocyanate, THF, RT; [14] f) phenyl, 4-iPr-phenyl, 4-tBuphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl or 3,4,5-trimethoxyphenyl isocyanate, THF, RT; [15] g) benzoyl, 3,4-dimethoxybenzoyl, 3,5-dimethoxybenzoyl, 3,4,5-trimethoxybenzoyl chloride, NaOH, H 2 O, CH 2 Cl 2 or Et 2 O, RT; [16,17] h) phenyl or 3,4-dimethoxyphenyl sulfonyl chloride, Et 2 O, H 2 O, NaOH, RT. [16] (PhthCl = 2-phthalimidoacetyl chloride).…”

Section: Resultsmentioning

confidence: 97%

“…The tripodal ligands contain urea, amido or sulfonamido hydrogen-bond donors, which are aligned to bind to the regions of greatest electron density along the faces and edges of the octahedral anion. The ligand structure incorporates a protonatable bridgehead nitrogen centre that pro- sphere and coordination complexes, [3] the very slow ligand exchange for the hexachloroplatinate anion, [PtCl 6 ] 2À , [4] makes it necessary to address and recognise the outer coordination sphere of this species to form neutral anion-ligand packages. Selectivity continues to be a challenge in the development of supramolecular recognition of anions, [5] and is a pervasive problem in extractive metallurgy because the generation of electrolytes of high purity is essential for efficient electrolytic reduction to produce metals.…”

Section: Introductionmentioning

confidence: 99%

“…3 JA C H T U N G T R E N N U N G (H,H) = 8.6 Hz; 6 H; H Ar ), 7.03 (d, 3 JA C H T U N G T R E N N U N G (H,H) = 7. JA C H T U N G T R E N N U N G (H,H) = 6.0 Hz, 3 H; H Ar ), 7.33 (t, 3 J-A C H T U N G T R E N N U N G (H,H) = 9.0 Hz; 6 H; H Ar ), 7.18 (br, 3 H; NH), 7.07 (t, 3 JA C H T U N G T R E N N U N G (H,H) = 9.0 Hz, 6 H; H Ar ), 3.60-3.55 (m, 6 H; CH 2 ), 2.76 ppm (t, 3 JA C H T U N G T R E N N U N G (H,H) = 6. [17] Compound L 11 was prepared by the treatment of tren with 3,4-dimethoxybenzoyl chloride by following procedure B.…”

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confidence: 97%

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Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry

Warr

Westra

Bell

et al. 2009

Chemistry A European J

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A series of tripodal receptors designed to recognise the outer coordination sphere of the hexachlorometallate anion [PtCl(6)](2-), and thus show selectivity for ion-pair formation over chloride binding, has been synthesised and characterised. The tripodal ligands contain urea, amido or sulfonamido hydrogen-bond donors, which are aligned to bind to the regions of greatest electron density along the faces and edges of the octahedral anion. The ligand structure incorporates a protonatable bridgehead nitrogen centre that provides a positive charge to ensure the solubility of a neutral 2:1 [LH](+)/[PtCl(6)](2-) complex in water-immiscible solvents. The extraction of [PtCl(6)](2-) from acidic chloride solutions was evaluated by using a pH-swing mechanism to control the loading and stripping of the metallate anion. The ligands L(1)-L(3), L(5)-L(9), L(11)-L(13) and L(15) showed extremely high loading (up to 95% in some cases) and high selectivity for [PtCl(6)](2-) over chloride ions (present in a 60-fold excess) compared with trioctylamine, a model Alamine reagent, which, under identical conditions, only extracted 10% of the Pt(IV) anions. Generally, extraction was observed to be greater for urea-containing ligands than their amido analogues, and a quantitative recovery of platinum from feed solutions was achieved. The formation of neutral ([LH](+))(2)[PtCl(6)](2-) packages in organic media is supported by single-crystal X-ray structure determinations of [(L(2)H)(2)PtCl(6)] x 2 CH(3)CN, [(L(8)H)(2)PtCl(6)(MeOH)(2)], [(L(12)H)(2)PtCl(6)] x 2 CH(3)CN and [(L(14)H)(2)PtCl(6)], which confirm the presence of significant hydrogen bonding between the anion and urea or amido moieties of the protonated ligand and the anion. The structure of [(L(1)H)(H(3)O)PtCl(6)] x C(6)H(6) x CH(3)CN shows hydrogen bonding of a H(3)O(+) cation to the receptor and confirms that other stoichiometries are also possible, indicating that speciation in solution may be more complex.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 97%

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Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry

Warr

Westra

Bell

et al. 2009

Chemistry A European J

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“…4-6 Furthermore, electrostatic interactions between the targeted anion and a Lewis acidic metal centre can promote a binding event. 7;8 For example, in cascade complexes, first discovered by Lehn, 9 a binucleating capsular ligand was used to accommodate two metallic centers within the cavity, typically in a pseudo -pyramidal geometry with a vacant site. These complexes, in which the two metallic centers are held at a well-defined distance from one another, can then recognize an anion of the appropriate size as the result of bridging coordination interaction involving the two metal centers.…”

Section: Introductionmentioning

confidence: 99%

Selective Anion Binding by a Cofacial Binuclear Zinc Complex of a Schiff-Base Pyrrole Macrocycle

Devoille¹,

Richardson²,

Bill³

et al. 2011

Inorg. Chem.

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The synthesis of the new cofacial binuclear zinc complex [Zn2(L)] of a Schiff-base pyrrole macrocycle is reported. It was discovered that the binuclear microenvironment between the two metals of [Zn2(L)] is suited for the encapsulation of anions, leading to the formation of [K(THF)6][Zn2(μ-Cl)(L)].2THF and [Bun4N][Zn2(μ-OH)(L)] which were characterized by X-ray crystallography. Unusually obtuse Zn-X-Zn angles (X=Cl: 150.54(9)° and OH: 157.4(3)°) illustrate the weak character of these interactions and the importance of the cleft pre-organization to stabilize the host. In the absence of added anion, aggregation of [Zn2(L)] was inferred and investigated by successive dilutions and by the addition of coordinating solvents to [Zn2(L)] solutions using NMR spectroscopy as well as isothermal microcalorimetry (ITC). On anion addition, evidence for de-aggregation of [Zn2(L)], combined with the formation of the 1:1 host-guest complex, was observed by NMR spectroscopy and ITC titrations. Furthermore, [Zn2(L)] binds to Cl− selectively in THF as deduced from the ITC analyses, while other halides induce only de-aggregation. These conclusions were reinforced by DFT calculations, which indicated that the binding energies of OH− and Cl− were significantly greater than for the other halides.

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“…9,10 Furthermore, N-substituted mixed-donor crown ethers may find application as redox chemosensors 11,12 or as hosts for the simultaneous binding of anions and cations. 13,14 In this research work, new dinaphthosulfide aza crowns from 1-naphthol were prepared from the reaction of dinaphthalene diester and aliphatic diamines in methanol.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New 1-Naphthol Aza Oxa Thia Crowns

Rostami

2011

Phosphorus, Sulfur, and Silicon and the Related Elements

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New dinaphthosulfide aza oxa thia crowns from 1-naphthol were prepared. At first, 2,2 -thiobis(1-hydroxynaphthalene) (a dinaphthol) was prepared from 1-naphthol. Then diester was prepared from the reaction of dinaphthol and methylchloroacetate. Aza crowns were synthesized from the reaction of diester and diamines (ethylene diamine, 1,3-diaminopropane, 1,4-diaminobutane, and 1,6-diaminohexane) in methanol.

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Ditopic azathioether macrocycles as hosts for transition metal saltsElectronic supplementary information (ESI) available: full experimental details. See http://www.rsc.org/suppdata/cc/b1/b109486f/

Cited by 27 publications

References 13 publications

Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry

Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry

Selective Anion Binding by a Cofacial Binuclear Zinc Complex of a Schiff-Base Pyrrole Macrocycle

Synthesis of New 1-Naphthol Aza Oxa Thia Crowns

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Ditopic azathioether macrocycles as hosts for transition metal saltsElectronic supplementary information (ESI) available: full experimental details. See http://www.rsc.org/suppdata/cc/b1/b109486f/

Cited by 27 publications

References 13 publications

Selective Extraction and Transport of the [PtCl6]2−Anion through Outer‐Sphere Coordination Chemistry

Selective Extraction and Transport of the [PtCl6]2−Anion through Outer‐Sphere Coordination Chemistry

Selective Anion Binding by a Cofacial Binuclear Zinc Complex of a Schiff-Base Pyrrole Macrocycle

Synthesis of New 1-Naphthol Aza Oxa Thia Crowns

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Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry

Selective Extraction and Transport of the [PtCl₆]²⁻Anion through Outer‐Sphere Coordination Chemistry