Reactivity of 1,8-octanedithiol monolayers on Au(111): Experimental and theoretical investigation

Carot, M.L.; Esplandiu, M.J.; Cometto, Fernando P.; Patrito, E.M.; Macagno, V. A.

doi:10.1016/j.jelechem.2005.01.019

Cited by 50 publications

(81 citation statements)

References 47 publications

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“…Moreover, in a similar way to what has been observed for the ODT layer, the charge density is maintained constant at 79.4 ± 3 A/cm 2 . The charge density obtained for the ODT-SAM in this work is much lower to that reported of ∼109 C/cm 2 under slightly different experimental conditions [5,19]. These authors attribute the extra charge to the reduction, at the same potentials for monolayer desorption, of the disulfide species that are probably formed between adjacent terminal sulphur atoms when the monolayer is exposed to air during the transfer from the forming to the measurement solution.…”

Section: Preparation Of the Alkanedithiol Samcontrasting

confidence: 71%

“…The addition of a reductor as tri-n-butylphosphine prevents the formation of multilayers and allows the generation of well-ordered monolayers of the dithiol in which the molecules adopt a standing-up orientation [17]. However, some authors have found an electrochemical evidence of the existence of intralayer disulfide bonds and its dependence on dithiol chain length [5,18,19]. They have shown that ␣--dithiols monolayers have a higher stability than the alkanethiol partners due to the formation of disulfide bonds between the terminal surface atoms with the alkyl chains arranged in a parallel fashion.…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical characterization of a 1,8-octanedithiol self-assembled monolayer (ODT-SAM) on a Au(111) single crystal electrode

García-Raya

Madueño

Sevilla

et al. 2008

Electrochimica Acta

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Section: Preparation Of the Alkanedithiol Samcontrasting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Electrochemical characterization of a 1,8-octanedithiol self-assembled monolayer (ODT-SAM) on a Au(111) single crystal electrode

García-Raya

Madueño

Sevilla

et al. 2008

Electrochimica Acta

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“…The above results are different from the previous study, 48 in which the reductive charge more than that of a full monoalyer was observed. A partially formed intralayer disulfide bond on top of dithiol SAMs was proposed and the extra charge was suggested to be due to the dissociation of the disulfide bond.…”

Section: Results Andcontrasting

confidence: 99%

“…25,52,53 The control of formation condition such as using different solvent, removal of oxygen from SAMs formation solution were also suggested. [22][23][24][25]30,31,41,[47][48][49][50][51][54][55][56][57] Formation of disulfide bond through the terminated free thiols on top of dithiol SAMs were reported as well. [32][33][34][35]48,49 Those interlayer and intralayer disulfide linkage will result in the formation of multilayer and rearrangement of molecular configuration of dithiol molecules in the SAM, respectively.…”

Section: Introductionmentioning

confidence: 92%

“…[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]41,[45][46][47][48][49][50][51][52][53][54][55] In this upright molecular structure, the unbound thiol group is pendent with respect to the Au substrate and serves as the platform for the applications, such as the preparation of copper (I)-dithiol or CdS nanoparticle-dithiol multilayer thin films, the formation of multilayer through disulfide linkage spontaneously or electrochemically, the measurement of electron transfer through single molecule or the construction of metalmolecule-metal sandwich structure. 3,[22][23][24][25][26][27][30][31][32][33][34][35][36][37][38] However, the quality of those thiol terminated surface has been debated.…”

Section: Introductionmentioning

confidence: 99%

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1,n-Alkanedithiol (n = 2, 4, 6, 8, 10) Self-Assembled Monolayers on Au(111): Electrochemical and Theoretical Approach

Qu¹,

Kim²,

Lee³

et al. 2009

Bulletin of the Korean Chemical Society

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The structures of 1,n-alkanedithiol (n = 2, 4, 6, 8, 10) self-assembled monolayers (SAMs) on a Au(111) substrate were investigated by electrochemical measurements and theoretical calculations. The results of the experimental techniques indicated that the dithiols, except n = 2, showed an upright molecular structure in the SAMs, in which alkanedithiols were bound to the Au surface via only one thiol functionality and the other one faced up to the air. The results also suggested that the formed dithiol SAMs were densely packed and highly oriented. Except ethanedithiol, which was thought to form a bilayer, the reductive desorption peak potentials of 1,n-alkanedithiol (n = 4, 6, 8, 10) SAMs were more negative than those of the corresponding monothiol ones in 0.1 M KOH solutions. This illustrates that the dithiol SAMs had higher stability than the corresponding monothiol ones. The major part of the high stability may be attributed to the van der Waals interaction among the sulfur atoms on top of the dithiol SAMs. The molecular modeling calculation showed that the structures of dithiol SAMs were similar to those of the corresponding monothiol SAMs and that all the dithiol SAMs, except ethanedithiol, were more stable than the corresponding monothiol SAMs. The calculated energy differences between dithiol and monothiol SAMs decreased with the increment of alkyl-chain length.

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Selfassembly of α,ω‐dithiols on surfaces and metal dithiol heterostructures

Hamoudi

Esaulov

2016

Annalen der Physik

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α,ω-Dithiols present an interesting case of molecules with two reactive terminal -SH groups (HS-R-SH) that allow their use as binders between different metallic entities. They have thus been used in molecular electronics conduction measurements, in "nanogap" electrodes of interest in plasmonics, as building blocks of more complex structures such as metal intercalated superlattices and in the formation of metalized organic thin films, including doped graphene type films. There exist however many problems, because the molecules may end up in undesirable configurations with both thiol terminals bound to the same metal particle/substrate or link with other molecules to produce "multi-molecule" or "multilayer" structures. This report discusses various key questions on dithiol linking with metal surfaces and the quest of protocols of making problem free dithiol metal structures. It then describes the use of dithiols and their SAMs to produce various metal organic heterostructures useful for molecular electronics and formation of doped metalized organic thin films. We discuss the build up of these structures by self assembly and lithography, their chemical composition and functional properties.

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Reactivity of 1,8-octanedithiol monolayers on Au(111): Experimental and theoretical investigation

Cited by 50 publications

References 47 publications

Electrochemical characterization of a 1,8-octanedithiol self-assembled monolayer (ODT-SAM) on a Au(111) single crystal electrode

Electrochemical characterization of a 1,8-octanedithiol self-assembled monolayer (ODT-SAM) on a Au(111) single crystal electrode

1,n-Alkanedithiol (n = 2, 4, 6, 8, 10) Self-Assembled Monolayers on Au(111): Electrochemical and Theoretical Approach

Selfassembly of α,ω‐dithiols on surfaces and metal dithiol heterostructures

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