Exchange versus intercalation of n-dodecanethiol monolayers on copper in the presence of n-dodecaneselenol and vice versa

Fonder, Gregory J.; Delhalle, Joseph; Mekhalif, Zineb

doi:10.1016/j.apsusc.2009.11.059

Cited by 13 publications

(9 citation statements)

References 74 publications

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“…Diphenyl disulfide did not react reliably under the tarnishing conditions to produce the silver benzenethiolate. This observation is consistent with observations in the field of SAM research that n -alkylselenolates have higher affinities and stronger interactions with metal surfaces than thiolates. − …”

Section: Role Of Reagent Oxidation State On the Mechanism Of Coordina...supporting

confidence: 91%

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Tarnishing Silver Metal into Mithrene

et al. 2018

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Silver metal exposed to the atmosphere corrodes and becomes tarnished as a result of oxidation and precipitation of the metal as an insoluble salt. Tarnish has so poor a reputation that the word itself connotes corruption and disrespectability; however, tarnishing is a facile synthetic approach for preparing thin metal-sulfide films on silver or copper metal that might be exploited to prepare more elaborate materials with desirable optoelectronic properties. In this work, we prepare luminescent semiconducting thin films of mithrene, a metal–organic chalcogenolate assembly, by replacing the tarnish-causing atmospheric sulfur source with diphenyl diselenide. Mithrene, or silver benzeneselenolate [AgSePh]∞, is a crystalline solid that contains both an organic supramolecular phase and a two-dimensional inorganic coordination polymer phase. This compound gradually accumulates as the sole product of silver metal corrosion. The chemical reaction is carried out on metallic silver thin films and yields crystalline films with thicknesses ranging from 5 to 100 nm. We use the large-area films (>6 cm2) afforded by this method to measure the optical properties of this compound. The mild-temperature, wafer-scale processing of hybrid chalcogenolate thin films may prove useful in the application of hybrid organic–inorganic materials in semiconductor devices and hierarchical architectures.

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Section: Role Of Reagent Oxidation State On the Mechanism Of Coordina...supporting

confidence: 91%

“…Silver has an affinity for organosulfur − and organoselenium − reagents, both of which rapidly adsorb and form self-assembled monolayers (SAMs) on the reactive metal surface. To begin, we compare and contrast the known structures of silver benzeneselenolate SAMs with silver benzeneselenolate MOCHA …”

Section: Resultsmentioning

confidence: 99%

Tarnishing Silver Metal into Mithrene

et al. 2018

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“…Similar experiments on copper-supported monolayers of thiolates and selenolates did not show strong preferences for either chalcogen. 74,75 Substrates can also be engineered to promote exchange. 76,77 Place exchange between adsorbed thiolates is generally slow in full-coverage monolayers.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Exchange Reactions between Alkanethiolates and Alkaneselenols on Au{111}

et al. 2014

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When alkanethiolate self-assembled monolayers on Au{111} are exchanged with alkaneselenols from solution, replacement of thiolates by selenols is rapid and complete, and is well described by perimeter-dependent island growth kinetics. The monolayer structures change as selenolate coverage increases, from being epitaxial and consistent with the initial thiolate structure to being characteristic of selenolate monolayer structures. At room temperature and at positive sample bias in scanning tunneling microscopy, the selenolate–gold attachment is labile, and molecules exchange positions with neighboring thiolates. The scanning tunneling microscope probe can be used to induce these place-exchange reactions.

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“…Both aromatic [105][106][107][108][109][110] and aliphatic [103,104] selenols have been successfully employed. The synthesis and the physicochemical properties of alkaneselenol- [111,112] and benzeneselenol- [113] derived SAMs on Cu(100) surfaces, as well as the stability of n-dodecanethiol SAMs on Cu in the presence of competing n-dodecaneselenol, [114] have also been investigated.…”

Section: Scheme 42mentioning

confidence: 99%

Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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Exchange versus intercalation of n-dodecanethiol monolayers on copper in the presence of n-dodecaneselenol and vice versa

Cited by 13 publications

References 74 publications

Tarnishing Silver Metal into Mithrene

Tarnishing Silver Metal into Mithrene

Exchange Reactions between Alkanethiolates and Alkaneselenols on Au{111}

Synthesis and Applications of Organic Selenols

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