Direkte anlagerung von thiosulfat an polarisierte doppelbindungen

Kerber, Robert C.; Starnick, Jürgen

doi:10.1016/s0040-4039(01)99904-6

Cited by 8 publications

(2 citation statements)

References 2 publications

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“…Scheme outlines the synthetic pathway. The Bunte (thiosulfate) salt of 2-acrylamido-2-methyl-1-propanesulfonic acid was obtained by reacting it with Na 2 S 2 O 3 . , The sulfonic acid-functionalized, water-soluble Au cluster (SO3-MPC) was synthesized by borohydride (exothermic!) reduction of a 3:1 (mol/mol) mixture of the Bunte salt and chloroaurate in 6:1 water/acetic acid.…”

Section: Resultsmentioning

confidence: 99%

Water-Soluble, Sulfonic Acid-Functionalized, Monolayer-Protected Nanoparticles and an Ionically Conductive Molten Salt Containing Them

2001

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Sulfonic acid-functionalized monolayer-protected gold clusters (SO3-MPCs) have been synthesized by the reaction of the Bunte (thiosulfate) salt of 2-acrylamido-2-methyl-1-propanesulfonic acid (SO3) with tetrachloroaurate and borohydride in aqueous acetic acid. The nanoparticles produced have an average core diameter, obtained by transmission electron microscopy (TEM), of 2.2 ( 1.1 nm, and a 30 wt % ligand content, obtained by thermogravimetric analysis. These parameters, assuming an ideal closed-shell truncated octahedral nanoparticle, correspond to an average nanoparticle formula of Au314SO3111. Proton NMR, Fourier transform infrared (FTIR), and UV/vis spectroscopies are consistent with nanoparticle formation, and acid/base titrations are consistent with the strong acid character of the SO3-MPC monolayer. These nanoparticles add to a growing family of water-soluble MPCs. Synthesis of a salt of SO3-MPC with a polyether-tailed triethylammonium countercation yields an ionically conductive molten salt, which is studied by alternating current impedance spectroscopy in the solid state (neat melt) and solution form.Monolayer-protected gold clusters (MPCs) are becoming recognized for their diverse chemical and physical properties 1-5 and properties potentially relevant to nanoscale electronic devices, optic devices, magnetic materials, multifunctional catalysts, chemical recognition, and biosensors, 1,6-10 among others. Since Brust et al. 2a described the synthesis of isolable, stable, alkanethiolatepassivated gold nanoparticles, such nanoparticles have been functionalized by simple chemical transformations, 2-5,11-14 with a wide variety of structural units, including aromatic thiolates, 2b,11-13 ω-substituted alkanethiolates, 14a and polyhetero-ω-functionalized alkanethiolates. 14b These materials exhibit solubility in organic solvents of polarity correlated with that of the monolayers but lack water solubility, which is desirable for a variety of purposes including use in conjunction with biological systems. 15 Progress in designing water-soluble MPCs has been steady over the past several years and now includes MPCs with monolayers of tiopronin, 16a,b poly(ethylene glycol), 16c glutathione, 17 4-hydroxythiophenol, 2b,13b mercaptobenzoic acid, 11b and mercaptosuccinic acid. 18 Solubilities of 4-hydroxythiophenol, mercaptobenzoic acid, and mercaptosuccinic acid functionalized clusters are both limited and pH-dependent. Tiopronin [N-(2-mercaptopropionyl)glycine] and glutathione MPCs are freely water-soluble and the former additionally has been further functionalized by ligand place exchange and by amide coupling reactions of its carboxylic acid groups. 16b Small Au 55 clusters with strong acid ligands (Au 55 [PPh 2 C 6 H 4 SO 3 H]Cl 6 ) have been reported. 19 There has, however, been no well-characterized MPC reported with strong acid-functionalized thiolate ligand monolayers.In the field of molten salts known as polymer electrolytes, it is understood 20 that solid-state cation conductivity (1) (a) Schon, G.; Simon, U. C...

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Section: Resultsmentioning

confidence: 99%

Water-Soluble, Sulfonic Acid-Functionalized, Monolayer-Protected Nanoparticles and an Ionically Conductive Molten Salt Containing Them

2001

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“…Recently, Lukkari and co-workers reportedthat alkylthiosulfates (Bunte salts) can be used to generate 2D SAMs on flat gold surfaces under anaerobic conditions and that the resulting Au−sulfur ligation is indistinguishable (by XPS) from that formed by the reaction of Au surfaces with alkanethiols. They pointed out that alkylthiosulfates are readily prepared from halo-functionalized organic moieties and from terminal alkenes having electron-withdrawing groups. , The preparation of thiosulfate-functionalized organic compounds is also simpler and more versatile than that of thiols or disulfides, because the synthesis of the latter can require harsh conditions (e.g., strong acidic conditions, basic conditions, or reducing agents). The synthetic requirements are especially at issue when the thiolate to be attached to the MPC bears a fragile functional grouping or linkage.…”

Section: Introductionmentioning

confidence: 99%

Alkanethiolate-Protected Gold Clusters Generated from Sodium S-Dodecylthiosulfate (Bunte Salts)

et al. 2000

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A new synthesis for alkanethiolate-functionalized gold clusters derived from sodium S-dodecylthiosulfate is presented. The new clusters are analytically characterized by 1H NMR spectroscopy, X-ray photoelectron spectroscopy (XPS), Fourier transform infrared (FTIR) spectroscopy, high-resolution transmission electron microscopy (HRTEM), thermogravimetric analysis (TGA), and UV−vis absorption spectroscopy. These monolayer-protected clusters (MPCs) are indistinguishable in composition, monolayer architecture, and Au−sulfur bonding from those previously prepared from dodecanethiol using the Brust synthesis. One difference is that, for syntheses run under identical conditions, the average core dimensions for MPC products from sodium S-dodecylthiosulfate are somewhat larger. The average core size of MPCs synthesized from sodium S-dodecylthiosulfate is somewhat solvent-dependent, being smaller when they are made using toluene/H2O rather than THF/H2O.

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Sulfinate ions as nucleophiles

Okuyama

1990

Sulphinic Acids, Esters and Derivatives (1990)

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Direkte anlagerung von thiosulfat an polarisierte doppelbindungen

Cited by 8 publications

References 2 publications

Water-Soluble, Sulfonic Acid-Functionalized, Monolayer-Protected Nanoparticles and an Ionically Conductive Molten Salt Containing Them

Water-Soluble, Sulfonic Acid-Functionalized, Monolayer-Protected Nanoparticles and an Ionically Conductive Molten Salt Containing Them

Alkanethiolate-Protected Gold Clusters Generated from Sodium S-Dodecylthiosulfate (Bunte Salts)

Sulfinate ions as nucleophiles

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