Chiral Pinwheel Clusters Lacking Local Point Chirality

Sun, Kai; Shao, Tingna; Xie, Jiale; Meng, Lan; Yuan, Hongkuan; Xiong, Zuhong; Wang, Jun-Zhong; Liu, Ying; Xue, Qi‐Kun

doi:10.1002/smll.201200168

Cited by 17 publications

(16 citation statements)

References 41 publications

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“…A recent STM report by Xue and coworkers [93] revealed an intriguing pinwheel assembly of pentacene on Bi (111). The pinwheels consist of 36 molecules oriented with their molecular plane perpendicular to the surface.…”

Section: Perturbation Of Parity Eigenstates In 1927mentioning

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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Section: Perturbation Of Parity Eigenstates In 1927mentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

223

264

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“…[13][14][15] Chiral and achiral molecules can assemble into supramolecular chiral structures on the surface when the surface symmetry is broken. 16 Rubrene (5,6,11,12-tetraphenyltetracene, C 42 H 28 ), an axial chiral molecule that consists of a twisted tetracene backbone with four phenyl substituents symmetrically attached to the two sides of the backbone in the gas phase (Fig. 1a and b), has been widely employed in light-emitting diodes and field-effect transistors because of the higher charge carrier mobility of rubrene single crystals on the surface.…”

Section: Introductionmentioning

confidence: 99%

Absolute configuration and chiral self-assembly of rubrene on Bi(111)

Sun

Meng

Wang

2015

Phys. Chem. Chem. Phys.

Self Cite

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We investigated the chiral self-assembly of rubrene molecules on a semi-metallic Bi(111) surface using low-temperature scanning tunneling microscopy. The absolute configuration of isolated rubrene enantiomers was identified from high-resolution images. Two types of homochiral domains of rubrene monomers and hexamers were observed, respectively. For rubrene monomers, chiral separation was spontaneous with each chiral monomer appearing in their respective domain. For rubrene hexamers, two levels of organization chirality were recorded: one is six heterochiral rubrene molecules arranged alternatively in a rubrene hexamer; and the other is a homochiral arrangement of individual hexamers. After annealing at 350 K, a large area of supramolecular self-assembled L- and R-type triangular heterochiral hexamers was obtained at the narrow terrace of Bi(111). Moreover, a molecular chiral inversion from the L-(R-) type to the R-(L-) type occurs during the formation of the hexamer domain structure and can be attributed to the enhanced intermolecular interactions governed by the intensive intermolecular extrusion at the narrow terrace.

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“…In the past two decades, the on-surface bottom-up strategy of supramolecular self-assembly has opened up a promising vista for constructions of highly organized low-dimensional nanostructures with molecular precision and versatile functionalities, − which bears significant prospects for further applications including heterogeneous catalysis, nanoelectronics, or purely for fundamental science and art. − The delicate choices of metal atoms/molecular precursors and surfaces are at the heart of constructing desired surface nanostructures. Besides, various parameters, such as substrate temperature, − concentration, − molecular stoichiometric ratio if with multicomponents, − electrical stimulation, − and solvent effect, , have been demonstrated to play vital roles in the formation of self-assembled supramolecular architectures, which could also effectively result in diverse structural transformations.…”

mentioning

confidence: 99%

Competition between Hydrogen Bonds and Coordination Bonds Steered by the Surface Molecular Coverage

et al. 2017

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In addition to the choices of metal atoms/molecular linkers and surfaces, several crucial parameters, including surface temperature, molecular stoichiometric ratio, electrical stimulation, concentration, and solvent effect for liquid/solid interfaces, have been demonstrated to play key roles in the formation of on-surface self-assembled supramolecular architectures. Moreover, self-assembled structural transformations frequently occur in response to a delicate control over those parameters, which, in most cases, involve either conversions from relatively weak interactions to stronger ones (e.g., hydrogen bonds to coordination bonds) or transformations between the comparable interactions (e.g., different coordination binding modes or hydrogen bonding configurations). However, intermolecular bond conversions from relatively strong coordination bonds to weak hydrogen bonds were rarely reported. Moreover, to our knowledge, a reversible conversion between hydrogen bonds and coordination bonds has not been demonstrated before. Herein, we have demonstrated a facile strategy for the regulation of stepwise intermolecular bond conversions from the metal-organic coordination bond (Cu-N) to the weak hydrogen bond (CH···N) by increasing the surface molecular coverage. From the DFT calculations we quantify that the loss in intermolecular interaction energy is compensated by the increased molecular adsorption energy at higher molecular coverage. Moreover, we achieved a reversible conversion from the weak hydrogen bond to the coordination bond by decreasing the surface molecular coverage.

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Chiral Pinwheel Clusters Lacking Local Point Chirality

Cited by 17 publications

References 41 publications

Molecular chirality at surfaces

Molecular chirality at surfaces

Absolute configuration and chiral self-assembly of rubrene on Bi(111)

Competition between Hydrogen Bonds and Coordination Bonds Steered by the Surface Molecular Coverage

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