Molecular interactions between organized, surface-confined monolayers and vapor-phase probe molecules. 5. Acid-base interactions

Sun, Li; Crooks, Richard M.; Ricco, Antonio J.

doi:10.1021/la00031a027

Cited by 120 publications

(160 citation statements)

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“…In particular, it was shown that the amine forms a stable monolayer on the Au surface [33], using amine in liquid phase (as we did) as in vapour phase [35][36][37][38]. After that, the complexes are easily oxidized (this is a redox reaction) leading to the dissolution of the first metallic layer.…”

Section: Discussionmentioning

confidence: 80%

Is gold always chemically passive?

Aufray

Roche

2008

Applied Surface Science

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OATAO is an open access repository that collects the work of Toulouse researchers and makes it freely available over the web where possible. AbstractWhen epoxy-amine liquid mixtures are applied onto metallic substrates (such as Al, Ti, Sn, Zn, Fe, Cr, Cu, Ag, Ni, and Au), concomitant amine chemisorption and metallic surface dissolution occur, leading to organo-metallic complex formation. The interphase formation was studied, using two different amines as hardener (IsoPhoroneDiAmine and DiEthyleneTriAmine). If the complex concentration within the liquid amine or epoxyamine prepolymer was higher than its solubility limit, the complexes will crystallize. Sharp needle-like crystals were only observed with metal-IPDA organo-metallic complexes. A lot of metals are widely used as reactive substrates with gold as a reference, which is considered chemically inert. It is misleading, since it will be shown in this article that gold reacts with amine, just as the other metals.

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Section: Discussionmentioning

confidence: 80%

Is gold always chemically passive?

Aufray

Roche

2008

Applied Surface Science

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“…We have examined five types of chemical interactions that occur between monolayers and molecules: electrostatic binding, covalent linking, complexation interactions, proton transfer, and hydrogen bonding (9)(10)(11)(12)(13)(14). These interactions are five of the six tools presently in our "toolbox"; the sixth is a physical recognition strategy that is discussed later (6).…”

Section: Resultsmentioning

confidence: 99%

“…We have attempted to use scanning tunneling microscopy (STM) to directly image template-induced defects, but our results have been ambiguous for at least two reasons. First, there are many structures on the surface of SAM-covered Au substrates that appear by STM to be defect sites whether templates are present or not (27)(28)(29). We have recently shown that these features are due to monoatomic pits in the Au surface, and while not electroactive, they appear similar to intentionally formed defect sites (28).…”

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confidence: 99%

Synthesis and Characterization of Two-Dimensional Molecular Recognition Interfaces

Crooks

Chailapakul

Ross

et al. 1994

Interfacial Design and Chemical Sensing

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This document has been approved for public release and sale; N00179 its distribution is unlimited. ABSTRACT (Maximum200 words)We have used self-assembly chemistry to synthesize monolayer assemblies that function as molecular recognition interfaces. In the first part of this paper, we show that onecomponent self-assembled n-alkanethiol monolayers with carboxylic acid functionalized -endgroups specifically adsorb vapor-phase acid-terminated molecules via hydrogen bonding or vapor-phase amine-terminate molecules via proton-transfer interactions. In the second part, we demonstrate that two-component monolayers, which consist of inert n-alkanethiol framework moleculesanddefect-inducing templat• molecules, can discriminate between "--solution-phase probe molecules based on their physical and chemical characteristics. By electrochemically etching the defects and then imaging the resulting surface by scanning tunneling microscopy the defect sites can be indirectly visualized. 93-2922393 1-. We have used self-assembly chemistry to synthesize monolayer .7 assemblies that function as molecular recognition interfaces. In • Dist first part of this paper, we show that one-component selfassembled n-alkanethiol monolayers with carboxylic acid functionalized endgroups specifically adsorb vapor-phase acid-_.terminated molecules via hydrogen bonding or vapor-phase amineterminate molecules via proton-transfer interactions. In the second part, we demonstrate that two-component monolayers, which consist of inert n-alkanethiol framework molecules and defectinducing template molecules, can discriminate between solutionphase probe molecules based on their physical and chemical characteristics. By electrochemically etching the defects and then imaging the resulting surface by scanning tunneling microscopy the defect sites can be indirectly visualized.Molecular recognition is the selective binding of a probe molecule to a molecular receptor. This binding interaction relies on both non-covalent intermolecular chemical interactions, such as hydrogen bonding or van der Waals forces, and steric compatibility, such as size or shape inclusion. At present, a detailed understanding of molecular recognition phenomena is hindered primarily by two experimental problems. First, in many natural systems the receptor is a large, flexible, and complex molecule with many potential binding sites, and as a result it is difficult to quantify the specific types and magnitudes of interactions that lead to probe binding. Second, there are only a few analytical methods that are sufficiently specific and sensitive that they can be used for studying individual molecular interactions in bound probe/receptor complexes. These and other difficulties associated with natural systems have resulted in the synthesis of simpler model receptors and characterization of their interactions with probe molecules (1-3).Two general strategies have been used for synthesizing and characterizing model receptors and their complexes with probe molecules. The first is based on interactio...

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“…The scope of such studies has ranged from simple electrostatic, [98] hydrophobic, [99] or hydrogen bond±driven adsorption [100,101] through molecular recognition phenomena [102] to adsorption of cells and proteins. [13] Unfortunately, space limitations do not allow us to explore this topic in detail.…”

Section: Non-covalent Interactionsmentioning

confidence: 99%