Chemisorption induced chirality: glycine on Cu

Chen, Qiao; Frankel, Daniel; Richardson, Neville V.

doi:10.1016/s0039-6028(01)01593-x

Cited by 132 publications

(188 citation statements)

References 18 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: 86%

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

et al. 2009

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Section: Introductionsupporting

confidence: 86%

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

et al. 2009

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“…Fig. 4 F and G. Enantiomorphic ordering in supramolecular assemblies by prochiral, or even achiral molecules have been reported (27)(28)(29)(30). Upon adsorption of FTBC-C12 molecules on the achiral graphite surface, the domains with opposite chirality coexist across the whole surface and lead to local chirality.…”

Section: Ftbc-c4 Assemblymentioning

confidence: 86%

Structural selection of graphene supramolecular assembly oriented by molecular conformation and alkyl chain

Chen

Chen²,

Pan³

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

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Graphene molecules, hexafluorotribenzo[a,g,m]coronene with ncarbon alkyl chains (FTBC-Cn, n ‫؍‬ 4, 6, 8, 12) and Janus-type ''double-concave'' conformation, are used to fabricate self-assembly on highly oriented pyrolytic graphite surface. The structural dependence of the self-assemblies with molecular conformation and alkyl chain is investigated by scanning tunneling microscopy and density functional theory calculation. An interesting reverse face ''up-down'' way is observed in FTBC-C4 assembly due to the existence of hydrogen bonds. With the increase of the alkyl chain length and consequently stronger van der Waals interaction, the molecules no longer take alternating ''up-down'' orientation in their self-assembly and organize into various adlayers with lamellar, hexagonal honeycomb, and pseudohoneycomb structures based on the balance between intermolecular and molecule-substrate interactions. The results demonstrate that the featured ''double-concave'' molecules are available block for designing graphene nanopattern. From the results of scanning tunneling spectroscopy measurement, it is found that the electronic property of the featured graphene molecules is preserved when they are adsorbed on solid surface.graphene molecule ͉ Janus-type double-concave conformation ͉ scanning tunneling microscopy ͉ self-assembly A graphene molecules is composed of fused aromatic sets and is regarded as graphite subunit. After the success in theoretical prediction and experimental realization of graphene, graphene type molecules attract a great deal of interest (1-4). Their unique structures provide them promising potentials in micro/nano electronic devices (5-7). Continuous effort in chemical synthesis of graphene type molecules has produced various graphene molecules with the structures and properties beyond simple graphene. For example, polycyclic aromatic hydrocarbons (PAHs) compounds belong to a class of important functional graphene molecules (7,8). PAHs and their derivatives contain 2D subsections of graphene and show significant advantages, such as good solubility and ability to bear different chemical functionalities in their periphery with various electronic properties. These graphene molecules are promising candidates as building block for nanodevices through self-assembled architectures on 2D solid surfaces (9, 10).As a powerful tool for nanoscience and nanotechnology, scanning probe microscopy, in particular, scanning tunneling microscopy (STM) studies have produced images of the molecular self-assembly of graphene molecules at atomic/submolecular resolution, providing molecular understanding of intermolecular interactions and origin of their physical/chemical properties (11)(12)(13)(14). Because of their chemical structures, most of PAHs have a planar conformation and are inclined to form well-defined long-range self-assemblies on various substrates, such as gold and highly oriented pyrolytic graphite (HOPG). For examples, an alkyl-substituted PAH with D 2h symmetry and 78 carbon atoms in the aromatic core can se...

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“…Copper surfaces are often chosen as substrate because amino acids are stable onto copper up to about 500 K, 8 while transition metal substrates such as nickel are known to catalyse dissociation even at moderate temperature. 9 Glycine adsorbed on Cu(110) is one of the amino acid/ metal systems that has been more thoroughly investigated by diffraction techniques (LEED 10,11 , PhD 12 ), microscopy (STM 11,13 ), IR and X-ray spectroscopy (RAIRS 11,14 , NEXAFS 10 , XPS 8,10 ) as well as density functional theory (DFT). [15][16][17] More recently, other low-index copper surfaces such as Cu(311) have been considered for studying glycine selfassembly without footprint chirality.…”

Section: Introductionmentioning

confidence: 99%

“…Although glycine is not intrinsically chiral, when adsorbed on the Cu(110) surface it produces the same chiral footprint typical of alanine 11,20,21 and proline 2, 22-24 on this surface, so glycine can be used as a model to understand the assembly of more complex amino acids on Cu(110). 2,8,25 Even though the bonding, structure and long range arrangement of glycine on Cu(110) have been investigated by several groups using a wide range of experimental 8,13,14,26 and computational tools 15,17,27,28 , the energy barriers between adsorbed conformers and the dynamics of glycine surface diffusion are still largely unresolved. In this work we have investigated, using DFT calculations, the energy landscapes of glycine conformers with identical footprint chirality and possible reaction pathways that convert the footprint chirality.…”

Section: Introductionmentioning

confidence: 99%

Energy landscapes and dynamics of glycine on Cu(110)

Sacchi

Wales

Jenkins

2017

Phys. Chem. Chem. Phys.

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Amino acids adsorbed over single crystal metal surfaces have emerged as prototypical systems for exploring the properties that govern the development of long-range chirality in selfassembled monolayers (SAM) and supramolecular 2D networks. In this study, we characterise the self-assembly mechanism for glycine on the Cu (110) surface. This process occurs on a time scale that is too fast for most atomically resolved microscopic techniques, so the mechanism we propose here provides new insight for an important unexplored surface phenomenon.

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Chemisorption induced chirality: glycine on Cu

Cited by 132 publications

References 18 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

Structural selection of graphene supramolecular assembly oriented by molecular conformation and alkyl chain

Energy landscapes and dynamics of glycine on Cu(110)

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