Assembly of a Chiral Amino Acid on an Unreactive Surface: (<i>S</i>)-Proline on Au(111)

Seljamäe-Green, Riho T.; Simpson, Grant J.; Grillo, Federico; Greenwood, John; Francis, S.M.; Schaub, Renald; Lacovig, Paolo; Baddeley, Christopher J.

doi:10.1021/la500336c

Cited by 20 publications

(57 citation statements)

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“…We have previously investigated the adsorption of (S)-proline on Au(111) 30 Chambliss et al 31 Subsequently, Meyer et al 47 showed that the nucleation proceeds via a place exchange mechanism whereby a single gold atom is displaced by a diffusing Ni atom which acts as a nucleation point for island formation. Figure 3 shows a series of STM images (acquired after the sample was cooled to ~77 K) recorded as a function of annealing temperature following a 0.8 L dose of (S)-proline at 300 K onto 0.15 ML Ni/Au(111) (larger images are available in the Supporting Information, Figure S1).…”

Section: Resultsmentioning

confidence: 99%

“…30 The intensity and BE of the 288.3 eV peak stays essentially constant with increasing annealing temperature.…”

Section: Xpsmentioning

confidence: 92%

“…Trimeric features of this type of structure were never observed following proline adsorption on Au(111), 30 hence the molecular array is stabilized by the presence of Ni. Most commonly, amino acids deprotonate on single crystal metal surfaces and adsorb in the anionic form 10,54,55 and the annealing temperature required to form the HP phase is significantly above the desorption temperature of H 2 from either Ni or Au surfaces.…”

Section: Xpsmentioning

confidence: 97%

“…Each of these peaks contain contributions from two components by analogy with the study on Au(111). 30 The larger peak contains contributions from components of similar intensity at 286.1 and 285.3 eV (corresponding to carbon atoms of the pyrrolidine ring), with a small low BE peak at 284.0 eV. After annealing to 390 K, the component at 286.1 eV becoming relatively more intense whilst the component at 285.3 eV becomes less intense.…”

Section: Xpsmentioning

confidence: 98%

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Formation of Bioinorganic Complexes by the Corrosive Adsorption of (S)-Proline on Ni/Au(111)

et al. 2014

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Nickel nanoparticles modified by the adsorption of chiral amino acids are known to be effective enantioselective heterogeneous catalysts. The leaching of nickel by amino acids has a number of potential effects including the induction of chirality in the nickel atoms left behind in the nanoparticle and the creation of catalytically active nickel complexes. The adsorption of (S)-proline onto Au(111) precovered by two dimensional nickel nanoclusters was investigated by scanning tunnelling microscopy, X-ray photoelectron spectroscopy and high resolution electron energy loss spectroscopy. Adsorption of (S)-proline at 300 K resulted in the corrosion of the nickel clusters, the oxidation of the leached nickel and the on-surface formation of bioinorganic complexes, which are concluded to contain three prolinate species in an 2 octahedral arrangement around the central Ni ion. Two distinguishable forms of nickel prolinate complexes were identified. One form self-assembles into 1-D chains and the other form gives rise to porous 2-D islands. Octahedral complexes of the type M(AB) 3 are intrinsically chiral resulting in two pairs of enantiomers. The mirror symmetry of each pair of enantiomers is broken when, as in this study, the bidentate ligand itself possesses a chiral center. DFT calculations are used to examine the relative energies of each Ni(prolinate) 3 complex as isolated gas phase species and isolated adsorbed species.

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Section: Resultsmentioning

confidence: 99%

“…30 The intensity and BE of the 288.3 eV peak stays essentially constant with increasing annealing temperature.…”

Section: Xpsmentioning

confidence: 92%

Section: Xpsmentioning

confidence: 97%

Section: Xpsmentioning

confidence: 98%

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Formation of Bioinorganic Complexes by the Corrosive Adsorption of (S)-Proline on Ni/Au(111)

et al. 2014

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“…the mirror equivalent surface azimuthal direction to the <1-54> direction, were ever observed in these experiments, providing evidence that (S)-lysine causes chiral faceting of the Au surface. The interaction of proline with the Au(111) surface has also been recently investigated by the same group by means of STM, XPS and HREEL spectroscopy [159]. It was shown that Pro is able to adsorb onto Au(111) at 300 K forming a 2D gas which condenses into self-assembled structures upon cooling to 77 K. Nucleation occurs at surface defects such as step edges and soliton boundaries (e.g.…”

Section: Ii)mentioning

confidence: 99%

Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

Costa

Pradier

Tielens

et al. 2015

Surface Science Reports

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Understanding the bio-physical-chemical interactions at nanostructured biointerfaces and the assembling mechanisms of so-called hybrid nano-composites is nowadays a keyissue for nanoscience in view of the many possible applications foreseen. The contribution of surface science in this field is noteworthy since, using a bottom-up approach, it allows the investigation of the fundamental processes at the basis of complex interfacial phenomena and thus it helps to unravelthe elementary mechanisms governing them. Nowadays it is well demonstrated that a wide variety of different molecular assemblies can form upon adsorption of small biomolecules at surfaces. The geometry of such self-organized structures can often be tuned by a careful control of the experimental conditions during the deposition process. Indeed an impressive number of studies exist (both experimental and -to a lesser extendtheoretical), which demonstrate the ability of molecular self-assembly to create different structural motifs in a more or less predictable manner, by tuning the molecular building blocks as well as the metallic substrate. In this frame, amino acidsand small peptides at surfaces are key, basic, systems to be studied. The amino acidsstructure is simple enough to serve as a model for the chemisorption of biofunctional molecules, but their adsorption at surfaces has applications in surface functionalization, in enantiospecific catalysis, biosensing, nanoparticles shape control or in emerging fields such as "green" corrosion inhibition. In this paper we review the most recent advancements in this field. We will start from amino acids adsorption at metal surfaces and we will evolve then in the direction of more complex systems, in thelight of the latest improvements of surface science techniques and of computational methods. On one side, we will focus on amino acids adsorption at oxide surfaces, on the other on peptide adsorption both at metal and oxide substrates. Particular attention will be drawn to the added value provided by the combination of several experimental surface science techniques and to the precious contribution of advanced complementary computational methods to resolve the details of systems of increased complexity. Finally, some hints into experiments performed in the presence of water and then characterized in UHV and in the related theoretical work will be presented. This is a further step towards abetter approximation of real biological systems. However, since the methods employed are often not typical of surface science, this topic is not developed in details.2

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Asymmetric Adsorption on Achiral Substrates

2018

Chirality at Solid Surfaces

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Assembly of a Chiral Amino Acid on an Unreactive Surface: (S)-Proline on Au(111)

Cited by 20 publications

References 58 publications

Formation of Bioinorganic Complexes by the Corrosive Adsorption of (S)-Proline on Ni/Au(111)

Formation of Bioinorganic Complexes by the Corrosive Adsorption of (S)-Proline on Ni/Au(111)

Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

Asymmetric Adsorption on Achiral Substrates

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