Dipolar Side Chain Control of Monolayer Morphology: Symmetrically Substituted 1,5-(Mono- and diether) Anthracenes at the Solution−HOPG Interface

Tong, Wenjun; Wei, Yongliang; Armbrust, Kurt W.; Zimmt, Matthew B.

doi:10.1021/la803811w

Cited by 22 publications

(22 citation statements)

References 47 publications

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“…The fact that, even in the high resolution images of Figure 4, no interstices can be found to pinpoint the termini of 1 in the assembly suggests a conformal contact through multiple interactions of p-p stacking and/or dipole-dipole attractions. This rationale is supported by recent studies by Wei et al [71][72][73][74] and Tahara and co-workers, [75] who showed that dipolar interactions provide directionality and stabilize a two-dimensional molecular pattern on a solid surface.…”

Section: Resultsmentioning

confidence: 59%

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Lee

Lin

Liao

et al. 2009

Chemistry A European J

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Self-assembly at the molecular level in solutions or on a surface is a subject of current interest. Herein we describe the tailoring of oligobisnorbornene 1, which represents an innovative concept of a preorganized building block on the tens of nanometer scale. The rodlike 1 has vinyl and styrenyl end groups. Scanning tunneling microscopy (STM) reveals that the oligomers aggregate anisotropically along the long axis and form a one-dimensional assembly in which, remarkably, no interstitial gap appears between neighboring oligomers. Dynamic light-scattering (DLS) measurements indicate that the assembly develops in solution. With a shear treatment for dropcast films, a unidirectionally ordered domain with a defect density less than 0.5 % can be prepared. Simulation results by molecular dynamics suggest that there may be multiple interactions such as pi-pi stacking and dipolar attractions taking place between the termini of the oligomers. To demonstrate the importance of double bonds in the oligomeric backbones and termini towards the tectonic assembly, a hydrogenated analogue was synthesized; pi-pi interactions are thus less significant and the film morphology is completely different from that of 1. This work extends the concept of molecular tectonics to preorganized oligomers and opens up a new avenue of nanopatterning toward nanodevices.

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Section: Resultsmentioning

confidence: 59%

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Lee

Lin

Liao

et al. 2009

Chemistry A European J

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“…van der Waals (vdW) interactions of long alkyl chains , and hydrogen bonding (H-bonding) − are the two most often used interactions to control the structures of SAMNs. However, metal coordination, , halogen bonding (X-bonding), − and dipole–dipole interactions ,− have also been explored in affecting and tailoring their structural configurations. Shape complementarity is another important factor, which has been creatively explored in the design of complex multicomponent SAMNs (see below) …”

Section: Self-assembled Molecular Networkmentioning

confidence: 99%

Supramolecular Assemblies on Surfaces: Nanopatterning, Functionality, and Reactivity

et al. 2018

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Understanding how molecules interact to form large-scale hierarchical structures on surfaces holds promise for building designer nanoscale constructs with defined chemical and physical properties. Here, we describe early advances in this field and highlight upcoming opportunities and challenges. Both direct intermolecular interactions and those that are mediated by coordinated metal centers or substrates are discussed. These interactions can be additive, but they can also interfere with each other, leading to new assemblies in which electrical potentials vary at distances much larger than those of typical chemical interactions. Earlier spectroscopic and surface measurements have provided partial information on such interfacial effects. In the interim, scanning probe microscopies have assumed defining roles in the field of molecular organization on surfaces, delivering deeper understanding of interactions, structures, and local potentials. Self-assembly is a key strategy to form extended structures on surfaces, advancing nanolithography into the chemical dimension and providing simultaneous control at multiple scales. In parallel, the emergence of graphene and the resulting impetus to explore 2D materials have broadened the field, as surface-confined reactions of molecular building blocks provide access to such materials as 2D polymers and graphene nanoribbons. In this Review, we describe recent advances and point out promising directions that will lead to even greater and more robust capabilities to exploit designer surfaces.

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“…12 Multiple phases were often observed on the same sample. 13,14 One would expect, however, that if dipolar interactions were indeed driving the molecular self-assembly then only one final configuration, one that represents the electrostatic minimum, would be observed for dipolar molecules. As is evident from the brief review above, this is clearly not the case.…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of strongly dipolar molecules on metal surfaces

Kunkel

Hooper

Simpson

et al. 2015

The Journal of Chemical Physics

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The role of dipole-dipole interactions in the self-assembly of dipolar organic molecules on surfaces is investigated. As a model system, strongly dipolar model molecules, p-benzoquinonemonoimine zwitterions (ZI) of type C 6 H 2 (· · · NHR) 2 (· · · O) 2 on crystalline coinage metal surfaces were investigated with scanning tunneling microscopy and first principles calculations. Depending on the substrate, the molecules assemble into small clusters, nano gratings, and stripes, as well as in two-dimensional islands. The alignment of the molecular dipoles in those assemblies only rarely assumes the lowest electrostatic energy configuration. Based on calculations of the electrostatic energy for various experimentally observed molecular arrangements and under consideration of computed dipole moments of adsorbed molecules, the electrostatic energy minimization is ruled out as the driving force in the self-assembly. The structures observed are mainly the result of a competition between chemical interactions and substrate effects. The substrate's role in the self-assembly is to (i) reduce and realign the molecular dipole through charge donation and back donation involving both the molecular HOMO and LUMO, (ii) dictate the epitaxial orientation of the adsorbates, specifically so on Cu(111), and (iii) inhibit attractive forces between neighboring chains in the system ZI/Cu(111), which results in regularly spaced molecular gratings. C 2015 AIP Publishing LLC. [http://dx

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Dipolar Side Chain Control of Monolayer Morphology: Symmetrically Substituted 1,5-(Mono- and diether) Anthracenes at the Solution−HOPG Interface

Cited by 22 publications

References 47 publications

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Supramolecular Assemblies on Surfaces: Nanopatterning, Functionality, and Reactivity

Self-assembly of strongly dipolar molecules on metal surfaces

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