Two-dimensional chirality at liquid–solid interfaces

Elemans, Johannes A. A. W.; Cat, Inge De; Xu, Hong; Feyter, Steven De

doi:10.1039/b800403j

Cited by 219 publications

(179 citation statements)

References 45 publications

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“…Many unique molecular assembly structures, including host-guest complexes, multi-component hydrogen-bonded networks and chiral assemblies, have been fabricated in a controlled way. Readers who are interested in assemblies of organic functional molecules are referred to previous reviews [5][6][7][8][9]. The applications of the STM method in studies of biomolecules also have fascinated many researchers for its high structural resolution without complicated sample preparation, for instance single crystal growth, and for its sensitivity to electronic structure of the molecules.…”

Section: Introductionmentioning

confidence: 99%

Single-molecule studies on individual peptides and peptide assemblies on surfaces

Yang

Wang

2013

Phil. Trans. R. Soc. A.

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This review is intended to reflect the recent progress in single-molecule studies of individual peptides and peptide assemblies on surfaces. The structures and the mechanism of peptide assembly are discussed in detail. The contents include the following topics: structural analysis of single peptide molecules, adsorption and assembly of peptides on surfaces, folding structures of the amyloid peptides, interaction between amyloid peptides and dye or drug molecules, and modulation of peptide assemblies by small molecules. The explorations of peptide adsorption and assembly will benefit the understanding of the mechanisms for protein-protein interactions, protein-drug interactions and the pathogenesis of amyloidoses. The investigations on peptide assembly and its modulations could also provide a potential approach towards the treatment of the amyloidoses.

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Section: Introductionmentioning

confidence: 99%

Single-molecule studies on individual peptides and peptide assemblies on surfaces

Yang

Wang

2013

Phil. Trans. R. Soc. A.

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“…The long-standing discussion concerning the fundamental origins of biomolecular homochirality has been one of several motivations for a wide variety of studies into the adsorption and organization of chiral molecules on welldefined single-crystal surfaces which have been performed during the last decade [26][27][28][29][30][31][32]. These studies have in particular relied on local-probe scanning tunneling microscopy (STM) which allows molecular and supramolecular chirality to be directly observed.…”

Section: Introductionmentioning

confidence: 99%

Chiral Symmetry Breaking Observed for Cysteine on the Au(110)-(1×2) Surface

2011

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A pronounced enantiomeric excess of LL-cysteine dimers is observed by scanning tunneling microscopy (STM) on the Au (110)- (192) surface after partial thermal desorption/decomposition of racemic cysteine. We systematically examine several possible origins for this intriguing observation of chiral symmetry breaking, including a chiral bias of the substrate, but remain unable to identify the source.

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“…Among various molecular nanostructures, two-dimensional surface chirality is a property of asymmetry and of great interest in fundamental research and industrial application such as life genesis, nonlinear optics, enantioselective heterogeneous catalysis, and surface modification (1)(2)(3). With atomic resolution, scanning tunneling microscopy (STM) is powerful in surface chirality study (4)(5)(6)(7). From absolute chirality determination to chiral structure fabrication with chiral molecules or achiral molecules on a solid surface, a few results have been reported (8)(9)(10)(11)(12)(13).…”

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confidence: 99%

Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy

Chen

Wang

et al. 2010

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

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OPV3-CHO molecules are employed to prepare assembly on highly oriented pyrolytic graphite, and the so-prepared assembly is investigated by scanning tunneling microscopy. In the assembly chiral domains are observed with various structures such as linear and windmill. The chiral structural formation, stability, transition, and possible unification are intensively studied. After thermal annealing, linear structure was the only structure. To achieve a unified assembly with a single structure, an efficient method is proposed by coadsorption of OPV3-CHO with selected molecules. For example, an assembly with side-by-side helix structure is formed by a simple coadsorption of OPV3-CHO with alkyl bromide (C n H 2nþ1 Br, n ¼ 15-18). The experiments by cocrystallization of OPV3-CHO∕ C n H 2nþ1 X (X ¼ Cl, Br, and I) show the important role of halogen bonding in formation of the uniform structure. The results are significant in understanding the intermolecular noncovalent interactions that dominate the surface structure and chirality.coadsorption | halogen bonding | surface chirality U nderstanding the formation and structural transition of molecular nanostructure is an important issue in chemistry, molecular science, and nanodevice fabrication. Among various molecular nanostructures, two-dimensional surface chirality is a property of asymmetry and of great interest in fundamental research and industrial application such as life genesis, nonlinear optics, enantioselective heterogeneous catalysis, and surface modification (1-3). With atomic resolution, scanning tunneling microscopy (STM) is powerful in surface chirality study (4-7). From absolute chirality determination to chiral structure fabrication with chiral molecules or achiral molecules on a solid surface, a few results have been reported (8-13). Xu et al. directly observed the chirality of (R)-and (S)-2-phenylpropionamide molecules on Cu(111) in solution by using electrochemical STM (14). De Feyter et al. studied solvent-induced homochirality in selfassembled monolayers of achiral molecules. The chirality of the solvent directs the macroscopic chirality of the monolayer (15). After these results, we focus on the current challenge in surface chirality, which includes understanding the underlying driving force for the chiral formation, amplification, transition, and controlling the chiral structure.Recently, oligo(p-phenylenevinylene) (OPV) and its derivatives have attracted a lot of attention because of their advanced optical and electronic properties and possible application in organic electronic devices (16)(17)(18). In the present report, an aldehyde-substituted OPV molecule (OPV3-CHO, Scheme 1) is used as a model compound to study its structure on a solid surface. It is found that achiral OPV3-CHO can form chiral domains on highly oriented pyrolytic graphite (HOPG). The OPV3-CHO adlayer is investigated by STM including structural formation, stability, transition, and possible unification of the chiral domains. The OPV3-CHO chiral domains appear in linear and windmil...

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Two-dimensional chirality at liquid–solid interfaces

Cited by 219 publications

References 45 publications

Single-molecule studies on individual peptides and peptide assemblies on surfaces

Single-molecule studies on individual peptides and peptide assemblies on surfaces

Chiral Symmetry Breaking Observed for Cysteine on the Au(110)-(1×2) Surface

Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy

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