Polymorphism in supramolecular chiral structures of R- and S-alanine on Cu(110)

Barlow, Susan; Louafi, S.; Roux, Delphine Le; Williams, J.; Muryn, Christopher A.; Haq, S.; Raval, Rasmita

doi:10.1016/j.susc.2005.06.015

Cited by 133 publications

(229 citation statements)

References 39 publications

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“…In both cases the methyl group protrudes towards the vacuum. The similarity to the conformations determined for Gly/Cu is evident, so that also for alaninate on Cu(110) very similar adsorption positions (near-on-top) were inferred [105] and then confirmed by DFT calculations [107] and photoelectron diffraction [108] for the 3 geometry. Figure 14.…”

Section: Alanine Adsorption At Cu Surfacessupporting

confidence: 63%

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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Section: Alanine Adsorption At Cu Surfacessupporting

confidence: 63%

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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“…overlayer lattice that has been observed and reported previously [4]. During subsequent heating the carboxylate layer decomposes at temperatures above 500 K with 'explosive' kinetics.…”

Section: Experimental Studies Of Adsorption Of Amino Acids On Copper supporting

confidence: 75%

Final Technical Report for DOE Grant DE-FG02-03ER15473 “Molecular Level Design of Heterogeneous Chiral Catalysis”

Sholl¹,

Gellman²

2007

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The production of enantiomerically pure chiral compounds is of great importance in the pharmaceutical industry. Although processes involving chiral catalysis and separations involving solid surfaces are known, the molecular-scale details of these processes are not well understood. This lack of understanding strongly limits the development of new chiral processes. Our collaborative research effort examines several intertwined aspects of chirality and enantioselectivity at catalytically active metal surfaces. At Carnegie Mellon, our efforts focus on the development of chirally imprinted metal powders as materials for chiral columns and the experimental and theoretical study of small chiral molecules adsorbed on well-characterized metal surfaces, both achiral and chiral. These efforts are being performed in close collaboration with our team members at the University of California Riverside and the University of Wisconsin Milwaukee.

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“…One of the four diastereomers is the enantiomer of one of the others. Such diastereoisomerism has been discussed controversially for the (2 Â 3) structure of alanine on Cu(110) [139][140][141][142][143][144]. As observed for the glycine (2 Â 3) structure, calculations for the pure enantiomers favor a structure including opposite footprints, as if the methyl group would have no influence.…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

223

264

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With the adsorption of larger molecules being increasingly tackled by surface scientists, the aspect of chirality often plays a role. This paper gives a topical review of molecular chirality at surfaces and gives a phenomenological overview of different aspects of adsorption and self‐assembly of chiral and prochiral molecules and the principles of mirror‐symmetry breaking at a surface. After a brief introduction into the history of molecular chirality and the important role it played for understanding the spatial structure of molecules, definitions of chirality are presented. Topics treated here are principle ways to create single chiral adsorbates, chiral ensembles, and monolayers by achiral molecules, adsorption of intrinsically chiral molecules at achiral and chiral surfaces, long‐range symmetry breaking in two‐dimensional (2D) crystals due to additional chiral bias, chiral restructuring of solid surfaces under the influence of chiral molecules, switching the handedness of adsorbates, and chirality at the liquid/air interface. An outlook onto further potential research directions and recommendations for further reading, including nonsurface‐related sources of chiral topics completes this paper.

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Polymorphism in supramolecular chiral structures of R- and S-alanine on Cu(110)

Cited by 133 publications

References 39 publications

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

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

Final Technical Report for DOE Grant DE-FG02-03ER15473 “Molecular Level Design of Heterogeneous Chiral Catalysis”

Molecular chirality at surfaces

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