New Structure of <scp>l</scp>-Cysteine Self-Assembled Monolayer on Au(111):  Studies by In Situ Scanning Tunneling Microscopy

Xu, Qinghua; Li, Wan; Wang, Chen; Bai, Chunli; Wang, Zheng-Yu; Nozawa, Tsunenori

doi:10.1021/la010670y

Cited by 79 publications

(96 citation statements)

References 25 publications

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“…These strong interactions comprising the hydrogen bonds between carboxylic and amino groups play a crucial role in the structure of cysteine adlayers. 5,6 On the other hand, at more positive potential values the same band that is observed at 890 cm -1 is not sensitive to chirality. This observation is consistent with the conclusion drawn above from the SERS spectra, that cysteine molecules are adsorbed in this potential range in the zwitterionic form and interact with the Ag surface by NH 3 + (probably with mediation of Cl -anions) and COO -groups and this interaction determines the structure of the cysteine adlayer.…”

Section: Resultsmentioning

confidence: 57%

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Graff

Bukowska

2005

J. Phys. Chem. B

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The adsorption of both (L-and D-) enantiomeric forms of cysteine on the silver electrode surface was studied by surface-enhanced Raman scattering spectroscopy (SERS) as a function of electrode potential and pH value of the solution. It was demonstrated that at potentials more positive than -0.7 V (for pH 3) or -0.8 V (for pH 2 or lower), in acidic environment L-cysteine molecules are adsorbed mainly as P H (gauche) conformer, in zwitterionic form with the COO -groups close to the surface. At more negative potentials, NH 3 + groups deprotonate at the surface with simultaneous weakening of the interaction of the carboxylic groups with the surface. Spectroscopic evidence for at least partial protonation of the COO -groups at strongly acidic solutions was given by observing the CdO stretching band at frequency lowered by about 30 cm -1 in comparison with that observed for crystalline cysteine hydrochloride. It points to the considerable enhancement of the strength of hydrogen bonds and may be ascribed to the formation of cyclic L-cysteine dimers at the electrode surface. In neutral and alkaline solutions, adsorbed L-cysteine molecules have deprotonated amino groups at wide potential range. Similar spectroelectrochemical experiments were performed for D-cysteine and for a racemic mixture of D,L-cysteine. As expected, results for D-cysteine were similar to those for L-cysteine. However, for racemic mixture at acidic pH, the spectral effects corresponding to potential-induced transition from adsorbed zwitterions to neutral molecule were considerably smaller. This effect was discussed in terms of stereoselective dimerization of cysteine molecule at the electrode surface.

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Section: Resultsmentioning

confidence: 57%

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Graff

Bukowska

2005

J. Phys. Chem. B

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“…Each Hcy molecule appears as one bright and one dark spots. According to the literature [9,17], sulfur exhibits bright contrast. Therefore, the bright spot is assigned to sulfur and the dark one corresponds to amino and carboxyl groups.…”

Section: Adlayer Structure Of Hcymentioning

confidence: 91%

“…Additionally, as a thiol molecule, the self-assembled monolayers of cysteine molecules on gold substrates by sulfur-gold bonds were used to immobilize proteins [4][5][6], which has been employed to fabricate artificial protein arrays and biosensors. So the molecular feature and adlayer structures of cysteine on gold surfaces have been investigated by scanning tunneling microscopy (STM), spectroscopic techniques and secondary ion mass spectrometry [7][8][9][10][11][12]. Intramolecular and intermolecular hydrogen bonds play a role for the adlayer structures of cysteine molecules.…”

Section: Introductionmentioning

confidence: 99%

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Adlayer structures of dl-homocysteine and l-homocysteine thiolactone on Au(1 1 1) surface: an in situ STM study

Zhang

Wang

et al. 2004

Electrochimica Acta

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The adsorption of dl-homocysteine (Hcy) and l-homocysteine thiolactone (HTL) on Au(1 1 1) electrode was investigated in 0.1 M HClO 4 by cyclic voltammetry and in situ scanning tunneling microscopy (STM). Hcy and HTL molecules formed highly ordered adlayers on Au (1 1 1) surface. High-resolution STM images revealed the orientation and packing arrangement in the ordered adlayers. Hcy molecules formed (2 √ 3 × 3 √ 3)R30 • adlayer structure and H-bonds between carboxyl groups were assumed to be responsible for the origin of tail-to-tail or head-to-head molecular arrangement, while HTL molecules formed (4 × 6) adlayer structure, and two different orientations and appearances in the ordered adlayer were found. Structural models were proposed for the two adlayers.

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“…75 4.2.3 Thiol and disulfide groups: cysteine and cystine/ Au(111) give the same surface structure. As an important amino acid and the only -SH containing natural amino acid, assembling of cysteine monolayers on various substrates in different environments 72,118,[127][128][129][130][131][132] has attracted significant attention ever since their introduction. A variety of L-cysteine and cystine assembling conditions will be addressed in Sections 4.3 and 4.4.…”

Section: Effects Of Terminal Groups In Target Moleculesmentioning

confidence: 99%

Electrochemically controlled self-assembled monolayers characterized with molecular and sub-molecular resolution

Zhang

Welinder

Chi

et al. 2011

Phys. Chem. Chem. Phys.

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Self-assembled organization of functional molecules on solid surfaces has developed into a powerful and sophisticated tool for surface chemistry and nanotechnology. A number of reviews on the topic have been available since the mid 1990s. This perspective article aims to focus on recent development in the investigations of electronic structures and assembling dynamics of electrochemically controlled self-assembled monolayers (SAMs) of thiol containing molecules on gold surfaces. A brief introduction is first given and particularly illustrated by a Table summarizing the molecules studied, the surface lattice structures and the experimental operating conditions. This is followed by discussion of two major high-resolution experimental methods, scanning tunnelling microscopy (STM) and single-crystal electrochemistry. In Section 3, we briefly address choice of supporting electrolytes and substrate surfaces, and their effects on the SAM structures. Section 4 constitutes the major body of the article by offering some details of recent studies for the selected cases, including in situ monitoring of assembling dynamics, molecular electronic structures, and the key external factors determining the SAM packing. In Section 5, we give examples of what can be offered by theoretical computations for the detailed understanding of the SAM electronic structures revealed by STM images. A brief summary of the current applications of SAMs in wiring metalloproteins, design and fabrication of sensors, and single-molecule electronics is described in Section 6. In the final two sections (7 and 8), we discuss the current status in understanding of electronic structures and properties of SAMs in electrochemical environments and what could be expected for future perspectives.

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New Structure of l-Cysteine Self-Assembled Monolayer on Au(111): Studies by In Situ Scanning Tunneling Microscopy

Cited by 79 publications

References 25 publications

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Adlayer structures of dl-homocysteine and l-homocysteine thiolactone on Au(1 1 1) surface: an in situ STM study

Electrochemically controlled self-assembled monolayers characterized with molecular and sub-molecular resolution

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