Design and synthesis of heteroditopic aza-thioether macrocycles for metal extraction

Glenny, Mark W.; Lacombe, M.; Love, Jason B.; Blake, Alexander J.; Lindoy, Leonard F.; Luckay, Robert C.; Gloe, Karsten; Antonioli, Bianca; Wilson, Claire; Schröder, Martin

doi:10.1039/b609180f

Cited by 22 publications

(14 citation statements)

References 85 publications

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“…[1][2][3][4][5][6][7][8][9] Recent developments have focused on the recognition of heavy-metal salts such as nickel or copper sulfate for hydrometallurgical applications. [10][11][12] Welldesigned binding sites that combine electrostatic or hydrogen-bonding interactions enable ditopic host molecules to do this.…”

Section: Introductionmentioning

confidence: 99%

Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Reeske

Bradtmöller

Schürmann

et al. 2007

Chemistry A European J

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The synthesis of the crown-ether-substituted bis(organostannyl)methanes Ph(3)SnCH(2)Sn(Ph(2))-CH(2)-[16]crown-5 (1) and Ph(2)ISnCH(2)Sn(I)(Ph)-CH(2)-[16]crown-5 (2) is reported. Both compounds have been characterized by elemental analyses, (1)H, (13)C, (19)F, and (119)Sn NMR spectroscopy, and in the case of compound 2 also by electrospray ionization mass spectrometry. Single-crystal X-ray diffraction analysis revealed for the aqua complex 2.H(2)O trigonal-bipyramidal-configured tin atoms with intramolecular Sn(1)-O(1) and Sn(2)-O(1W) distances of 2.555(2) and 2.440(3) A, respectively. The water molecule is trapped in a sandwich-like fashion between the crown ether oxygen atoms O(2) and O(4) and the Sn(2) atom. NMR spectroscopy unambiguously proved the ability of compound 2 in acetonitrile to overcome the high lattice energy of sodium fluoride and to complex the latter under charge separation.

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Section: Introductionmentioning

confidence: 99%

Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Reeske

Bradtmöller

Schürmann

et al. 2007

Chemistry A European J

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“…[18,25] The AgÀ N and AgÀ S bond lengths in complexes 1-3 lie within the ranges 2.35-2.45 and 2.57-2.66 Å, respectively, and are similar to those observed in related silver(I) complexes with L 1 and L 3 derivatives. [26] In 3, the conformation adopted by L 3 upon coordination to the silver(I) centre does not allow the coordination of the oxygen donor atom and, therefore, the ligand imposes a tri-coordination to the metal ion rather than a tetra-coordination as observed for L 1 and L 2 in 1 and 2, respectively.…”

Section: Crystal Structuresmentioning

confidence: 96%

“…Interestingly, the Au(I)-Ag(I) distance of 2.662( 6 4) Å] compare well with those observed in 1-3 and in related silver(I) complexes with L 1 and L 3 derivatives. [26] The coplanar disposition of the perchlorophenyl rings in 4 allows the aurophilic interaction that leads to the formation of the Au 2 Ag 2 moiety, which is avoided in 3 due to the nearly orthogonal disposition of the aryl groups observed in this case.…”

Section: Crystal Structuresmentioning

confidence: 99%

Optical Properties in Heteronuclear Gold(I)/Silver(I) Complexes of Aliphatic Mixed‐Donor Macrocycles Featuring Metallophilic Interactions

et al. 2021

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The reaction of the polymeric heterometallic compound [{Au(C6Cl5)2}Ag]n with the macrocyclic ligands 1‐aza‐4,7,10‐trithiacyclododecane (L1), 1,7‐diaza‐4,11‐dithiacyclododecane (L2), 1‐aza‐4,10‐dithia‐7‐oxacyclododecane (L3) in tetrahydrofuran (THF) and 1 : 1 reaction molar ratio affords the new Au(I)/Ag(I) complexes [{Au(C6Cl5)2}{Ag(L1)}] (1), [{Au(C6Cl5)2}{Ag(L2)}] (2), [{Au(C6Cl5)2}{Ag(L3)}] (3) and [{Au(C6Cl5)2}{Ag(L3)}]2 (4) that have been structurally characterized. Despite 1–3 show the same nature of binuclear complexes, only 3 changes its luminescence properties upon grinding as a consequence of partial amorphization.

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“…A series of pendant arm aza-thioether macrocycles containing hydrogen-bonding amide functionalities have been synthesised of [12]aneS 3 N-CONHCOPh, [12] Figure 6. Membrane and liquid-liquid extraction experiments have shown that these systems are highly selective for Ag(I) over a range of other metal ions [104].…”

Section: Applicationsmentioning

confidence: 99%

Macrocyclic Assembly: A Dive into the Pecking Order and Applied Aspects of Multitalented Metallomacrocycles

Chaudhary

Rawat

2014

International Journal of Inorganic Chemistry

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To aid in knowledge of macrocyclic complexes and biomedical scientists, we are presenting here a review article with compilation of work done so far along in relation to macrocyclic ligands and their metal complexes. The metal ion chemistry of macrocyclic ligands has now become a major subdivision of coordination chemistry. This overview focuses on developments in design, synthesis, and self-assembly of metal-based architectures and ligands related to macrocyclic chemistry.

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Design and synthesis of heteroditopic aza-thioether macrocycles for metal extraction

Cited by 22 publications

References 85 publications

Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Solubilizing Sodium Fluoride in Acetonitrile: Synthesis, Molecular Structure, and Complexation Behavior of Bis(organostannyl)methyl‐Substituted Crown Ethers

Optical Properties in Heteronuclear Gold(I)/Silver(I) Complexes of Aliphatic Mixed‐Donor Macrocycles Featuring Metallophilic Interactions

Macrocyclic Assembly: A Dive into the Pecking Order and Applied Aspects of Multitalented Metallomacrocycles

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