Structure of enantiopure and racemic alanine adlayers on Cu(110)

Rankin, Rees B.; Sholl, David S.

doi:10.1016/j.susc.2004.10.025

Cited by 100 publications

(119 citation statements)

References 35 publications

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“…In all three of these cases, the acid is deprotonated by interaction with the Cu surface to form, respectively, glycinate (NH 2 CH 2 COO) and alaninate (NH 2 CH 3 CHCOO) species that bond to the surface through both of the carboxylate O atoms and the amino N atom, all three atoms occupying single-coordinated sites. This bonding configuration is consistent with a number of studies using electronic [7,8] and vibrational spectroscopy [9,10,11], and also scanning tunnelling microscopy [12,13,14,15,16,17] and density functional theory (DFT) calculations [18,19]. Some of these spectroscopic studies, however, do indicate that at different surface coverages, or in less well-ordered overlayers, other chemisorption bonding configurations probably occur involving only one or both of the carboxylate O atoms.…”

Section: Introductionsupporting

confidence: 87%

Adsorption structure of glycine on TiO2(1 1 0): A photoelectron diffraction determination

et al. 2009

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Section: Introductionsupporting

confidence: 87%

Adsorption structure of glycine on TiO2(1 1 0): A photoelectron diffraction determination

et al. 2009

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“…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. For the racemate the two enantiomers coexist in a single domain and remain true enantiomers by occupying the opposite footprint [141][142][143]. Basically, the same conclusion was made for racemic alanine on Cu(100) [142].…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 63%

“…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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“…Extensive experimental and theoretical studies have helped to shed light on the behavior of small amino acids deposited on clean surfaces under controlled conditions. [6][7][8][9][10] More recently, similar investigations have been extended to di-and tripeptides, 11,12 which represent a further step toward complex and realistic systems of biological relevance.…”

Section: Introductionmentioning

confidence: 99%

Structure and Energetics of Diphenylalanine Self-Assembling on Cu(110)

et al. 2007

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We investigate the dynamical features of the adsorption of diphenylalanine molecules on the Cu(110) surface and of their assembling into supramolecular structures by a combination of quantum and classical atomistic modeling with dynamic scanning tunneling microscopy and spectroscopic experiments. Our results reveal a self-assembling mechanism in which isolated adsorbed molecules change their conformation and adsorption mode as a consequence of their mutual interactions. In particular, the formation of zwitterions after proton transfer between initially neutral molecules is found to be the key event of the assembling process, which stabilizes the supramolecular structures. Because of the constraints on the intermolecular bonds exerted by the surface-molecule interactions, the assembly process is strictly stereoselective, and may suggest a general model for patterning and functionalization of bare metal surfaces with short chiral peptides.

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Structure of enantiopure and racemic alanine adlayers on Cu(110)

Cited by 100 publications

References 35 publications

Adsorption structure of glycine on TiO2(1 1 0): A photoelectron diffraction determination

Adsorption structure of glycine on TiO2(1 1 0): A photoelectron diffraction determination

Molecular chirality at surfaces

Structure and Energetics of Diphenylalanine Self-Assembling on Cu(110)

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