Thiol Terminated 1,4-Benzenedimethanethiol Self-Assembled Monolayers on Au(111) and InP(110) from Vapor Phase

Alarcón, L. Salazar; Chen, Lin; Esaulov, Vladimir A.; Gayone, J. E.; Sánchez, Esteban; Grizzi, O.

doi:10.1021/jp1044157

Cited by 37 publications

(30 citation statements)

References 63 publications

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“…42 The model of the BDMT film used to simulate reflectivity was elaborated on the basis of the insights obtained in previous studies by photoemission, angular-dependent XAS, infrared spectroscopy, SE, and electrochemistry. [30][31][32][33][34][35] In these works, it was derived that the molecules adopted a standing configuration at the Au surface with the formation of S-Au bonding.…”

Section: Resultsmentioning

confidence: 99%

“…[24][25][26][27][28][29] Moreover, in recent years we gained a detailed knowledge regarding the formation of BDMT SAMs on well-defined gold surfaces, exploiting both in-vacuum and in-liquid deposition, thanks to a systematic investigation by spectroscopic ellipsometry (SE), reflectionabsorption infrared spectroscopy, electrochemistry measurements, photoemission, and x-ray absorption (XAS). [30][31][32][33][34][35] We elaborated a reliable protocol 30,35 for obtaining single-layer films with molecules in a standing up configuration, with a sulfur headgroup bonded to the substrate and the other S-H unbound group pointing upright. The films in the present study were prepared according to this protocol.…”

Section: Introductionmentioning

confidence: 99%

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Structural and electronic properties of anisotropic ultrathin organic films from dichroic resonant soft x-ray reflectivity

et al. 2014

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We developed a quantitative approach for the determination of molecular arrangement and electronic structure in anisotropic organic ultrathin films based on the measurement of polarized reflectivity at the carbon K-edge. The reflectivity spectra were fitted to a parameterized model calculation. The method was applied to a self-assembled monolayer of 1,4-benzenedimethanethiol on gold. To simulate reflectivity, the organic anisotropic film was described by a dielectric tensor, obtained by ab initio calculations for the single molecule and suitable rotations to describe the molecular organization in film domains. Film structure was obtained though the best fit of the simulation to the experiment. Results were consistent with a monolayer-thick film composed of domains of molecules with in-plane isotropic distribution of orientations. In each domain, molecules adopted a standing configuration, with a tilt of 28° relative to the substrate normal. Information on the modification of the molecular electronic states due to chemical bonding was derived

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural and electronic properties of anisotropic ultrathin organic films from dichroic resonant soft x-ray reflectivity

et al. 2014

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“…15 The formation of SU dithiols has also been reported to occur from vapor phase. 16 4 However, a small amount of LD phase 12 as well as bicoordinated dithiols in a U-loop configuration 17 may also coexist with the SU phase. Short immersion times of a few seconds produce LD structures of 1,5-pentanedithiol whereas at long immersion times the SU structure is obtained.…”

Section: Introductionmentioning

confidence: 99%

The Role of Tris(2-carboxyethyl)phosphine Reducing Agent in the Controlled Formation of α,ω-Alkanedithiols Monolayers on Au(111) with Monocoordinated and Bicoordinated Configurations

et al. 2016

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The addition of the reducing agent tris(2-carboxyethyl) phosphine (TCEP) during the formation of α,ω-alkanedithiols monolayers on Au(111) using the immersion method produces the assembly of monolayers with bicoordinated molecules (both S-terminal groups bound to the surface) that have a reductive desorption potential that is more positive than for monolayers with monocoordinated molecules in a standing up configuration. We show that the use of TCEP either during formation of the monolayer or as a post treatment procedure allows the controlled formation of monolayers with bicoordinated or monocoordinated configurations. Density functional theory (DFT) calculations were performed to elucidate the role of TCEP in the formation of the bicoordinated configuration. We investigated the TCEP-dithiol interaction in ethanol solvent as well as the coadsorption of trimethylphosphine with 1,2-ethanedithiol on Au(111). The Brønsted base character of the phosphine facilitates the H exchange from the -SH groups of the dithiol to the phosphorus atom of TCEP with very low activation energy barriers, thus allowing the thiolate groups to bind to the Au(111) surface, thus yielding the bicoordinated configuration. Dithiol lifting mechanisms such as H exchange between S atoms and the formation of intra/inter layer disulfide bonds have much higher energy barriers.

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“…[38,39] The kinetics of adsorption and temperature induced desorption as well as information on structure can also be obtained in real time by ion scattering techniques such as low energy ion scattering (LEIS) and time of flight direct recoil spectroscopy (ToF DRS). [40] Surface Enhanced Raman Spectroscopy…”

Section: Characterization Processes: Determining the Presence Of Thiomentioning

confidence: 99%

Determination of Au Film Thiolation and Silane Bonding Onto SiO2 Films Within the Frame of Biosensor Surface Functionalization – an Analysis of Best Practices and Techniques

Bousiakou

Karapetis

2020

Croat. Chem. Acta

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This paper reviews some of the most common surface modification approaches in biosensing based on self-assembled monolayers with a particular focus on Au film thiolation and SiO2 film silanization. Such approaches are routinely used to alter the materials' surface properties towards a desired bioresponse. Furthermore, the most appropriate characterization methods towards ensuring successful surface modification are presented including XPS, HREELS, SPFS, Raman and FTIR spectroscopy as well as UPS with specific examples to demonstrate their importance. In addition, the mechanisms of fluorescent and non-fluorescent biotinylation of thiolated Au films and silanized SiO2 are discussed considering its importance in conjugating biomolecules such as enzymes, antibodies or chemokines onto surfaces, which carries high significance for biosensing applications. Finally, within this frame characterization routes towards ensuring effective attachment are discussed.

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Thiol Terminated 1,4-Benzenedimethanethiol Self-Assembled Monolayers on Au(111) and InP(110) from Vapor Phase

Cited by 37 publications

References 63 publications

Structural and electronic properties of anisotropic ultrathin organic films from dichroic resonant soft x-ray reflectivity

Structural and electronic properties of anisotropic ultrathin organic films from dichroic resonant soft x-ray reflectivity

The Role of Tris(2-carboxyethyl)phosphine Reducing Agent in the Controlled Formation of α,ω-Alkanedithiols Monolayers on Au(111) with Monocoordinated and Bicoordinated Configurations

Determination of Au Film Thiolation and Silane Bonding Onto SiO2 Films Within the Frame of Biosensor Surface Functionalization – an Analysis of Best Practices and Techniques

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