Aufbau supramolekularer Nanostrukturen an Oberflächen über Wasserstoffbrückenbindungen

Barth, Johannes V.; Weckesser, Jens; Cai, Chengzhi; Günter, Peter; Bürgi, Lukas; Jeandupeux, O.; Kern, Klaus

doi:10.1002/(sici)1521-3757(20000403)112:7<1285::aid-ange1285>3.0.co;2-0

Cited by 73 publications

(22 citation statements)

References 27 publications

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“…18 Self-assembly on metallic substrates in the conditions of ultra-high vacuum often results in appearance of chiral phases, 19,20 in particular characterized either by chiral clusters, chiral chains or 2D (extended) chiral domains. [21][22][23] These chiral assemblies can be stabilized by hydrogen bonding, but the origin of chirality mostly comes from the initial chirality of the molecules themselves. It is in particular the case of polyaromatic and heterocyclic compounds, 24,25 but also of the so-called bio-molecules like amino acids 26 or nucleic acid building blocks 27 which drive the research in the promising areas of biosensors and biomaterials.…”

Section: Introductionmentioning

confidence: 99%

“…carbonyl or carboxyl groups directly attached to the polyaromatic part of the molecule. 22,[28][29][30][31][32][33][34] The complexity of the possible output, including frequently appearing polymorphism of self-assemblies, usually renders difficult an accurate study of the balance between hydrogen bonds and molecule-substrate interactions for the determination of the molecular networks. Moreover, besides carboxyl group -the most frequently met functional group bearing the potential for hydrogen bonding formation, there exists interactions defined as weak hydrogen bonding which may involve N atoms in particular.…”

Section: Introductionmentioning

confidence: 99%

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Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

et al. 2016

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A hybrid disk-like/rod-like molecule comprising central triphenylene core symmetrically substituted with six azobenzene moieties (C-12) has been adsorbed at the 1,2,4trichlorobenzene/Au(111) interface, revealing the potential of azobenzene moieties for the control of 2D chiral networks. The C-12, which due to its complex molecular structure possesses a relatively large number of degrees of freedom, surprisingly forms monolayers of only one kind of structure, namely a hexagonal network of large period, 3.5 nm. By combining Scanning Tunneling Microscopy (STM) and DFT calculations, we evidence that this specific 2D-ordering is due to cooperative weak hydrogen bonds between neighboring azobenzenes and azobenzene-Au(111) interactions. The crystallographic network is hexagonal, but azobenzene-azobenzene pairing, associated with hydrogen bonding renders the network chiral with a chirality spanning all ranges, from the molecular C-12 configuration, the configuration of the azobenzene dimers and the rosette-like azobenzene network, to the C-12 network orientation on Au(111) rotated by ±8° from the main crystallographic direction Au<110>, depending on the handedness of the molecular network. This chiral 2D system thus paves the way for the formation of macroscopic 2D molecular crystals of unique handedness, if additional enantiomeric chiral dopants can be used.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

et al. 2016

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“…[1][2][3][4][5][6] One of the more frequently studied building blocks is BDA on Cu(001). 7,8 It has been reported that BDA-molecules reside on Cu(001) as deprotonated dicarboxylic species.…”

Section: Introductionmentioning

confidence: 99%

A low energy electron microscopy study of the initial growth, structure, and thermal stability of 4,4′-biphenyldicarboxylic acid domains on Cu(001)

Khokhar

Gastel

Schwarz

et al. 2011

The Journal of Chemical Physics

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The growth of 4,4(')-biphenyldicarboxylic acid (BDA) on Cu(001) has been studied using low energy electron microscopy and selective area low energy electron diffraction. The emergence of large islands and hydrogen bonding to perpendicularly oriented, adjacent molecules is confirmed. The two benzene rings of adsorbed BDA are twisted along the molecular axis. Unconventional growth of the domains, followed by a second nucleation stage, is observed at room temperature. This unanticipated feature is attributed to the accumulation of stress in the islands. Ostwald ripening in the films and the decay of BDA domains at 448 K exhibits features that are consistent with diffusion limited behavior.

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“…An excellent method to visualize these nanostructures with submolecular resolution on, for example, highly ordered pyrolytic graphite (HOPG) is represented by scanning tunneling microscopy (STM). − In the past few years, an increasing number of references on self-assembly processes was found where hydrogen bonding was used as a directional tool for the design of superstructures on surfaces from tailored subunits. In addition to a few examples where weak hydrogen bonds C−H···X (X = N, O) − were employed as structurally directing motif, strong hydrogen bonds X−H···Y (X, Y = N, O, S) are dominating self-organization processes based on directional intermolecular forces. Apart from biological molecules such as, for example, nucleobases, , synthetic molecules are utilized for self-assembly on surfaces investigated by STM.…”

Section: Introductionmentioning

confidence: 99%

Homo- and Heteroassemblies of Lactim/Lactam Recognition Patterns on Highly Ordered Pyrolytic Graphite: An STM Investigation

et al. 2006

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The 2D assembly of phthalhydrazide 1 and aminopyrimidine 2 derivatives equipped with C16 and C8 alkyl chains, respectively, on highly ordered pyrolytic graphite (HOPG) was studied by scanning tunneling microscopy. Well-defined, rather complex surface layer patterns emerge resulting from a delicate balance of (self-) complementary (strong) hydrogen bonds and van der Waals force-driven ordering of the alkyl substituents on the HOPG surface. The four different compounds and their 1:1 mixtures yield seven different 2D structures. Phthalhydrazide offers in principle three tautomeric forms, with the lactim/lactam being the most stable. Depending on the solvent, different morphologies can be obtained. In one case, the special self-assembly of achiral 1a leads to a 2D chiral packing with the left- and right-hand motifs present in different domains. We assume that pure 1a is expressed in its lactim/lactam form, whereas in a 1:1 mixture with 2a it switches to the bislactam form. These features display a process of dynamic diversity generation through tautomerism resulting in different nanostructures in response to environmental parameters.

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Aufbau supramolekularer Nanostrukturen an Oberflächen über Wasserstoffbrückenbindungen

Cited by 73 publications

References 27 publications

Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

A low energy electron microscopy study of the initial growth, structure, and thermal stability of 4,4′-biphenyldicarboxylic acid domains on Cu(001)

Homo- and Heteroassemblies of Lactim/Lactam Recognition Patterns on Highly Ordered Pyrolytic Graphite: An STM Investigation

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