Chain‐length‐adjusted assembly of substituted porphyrins on graphite

Wang, Hongna; Wang, Chen; Zeng, Qingdao; Xu, Shaojian; Yin, Shuxia; Xu, Bo; Bai, Chunli

doi:10.1002/sia.1051

Cited by 46 publications

(46 citation statements)

References 22 publications

(5 reference statements)

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“…30,33 In contrast to P1 monolayer where intermolecular H-bonding lead to the formation of faceon architecture, P2 molecules adopt edge-on arrangement as steered by van der Waals interactions and π-π stacking. Typically, the porphyrin derivatives equipped with long alkyl chains are physisorbed flat in face-on fashion on the graphite surface, where the self-assembled structures can be stabilized by both porphyrin core/HOPG and alkyl chain/HOPG van der Waals interactions.…”

Section: Resultsmentioning

confidence: 99%

“…When spatial confinement in 2D on a solid substrate is employed, this approach makes it possible to generate periodically ordered structures, which can then be characterized on the nanoscale by Scanning Tunneling Microscopy (STM). [30][31][32][33][34][35][36] In general, the adsorption of porphyrins can be classified into two distinct molecular configurations, i.e. [22][23] Porphyrins have been extensively explored as molecular scaffolds because of their unique opto-electronic properties, which makes them appealing for numerous applications including solar cells 24 and photo-catalysis.…”

Section: Introductionmentioning

confidence: 99%

“…[4][5][6][7][8][9][10][11][12][13][14][15][16] Self-assembly at interfaces enables the controlled positioning of functional units with sub-nanometer precision over areas of micrometers and thereby allows the fine-tuning of numerous properties of the resulting nanostructures [17][18][19][20][21] for technological applications, in particular in optics, catalysis, electronics and sensing. 30,33,[37][38][39][40] Conversely, when the intermolecular van der Waals interactions are stronger than those between molecules and substrate, the molecules tend to adopt an edge-on configuration. 25 STM was used to explore the self-assembly of porphyrins under ultra-high vacuum (UHV) on graphite 26 and metallic substrates [27][28][29] , and under ambient conditions on graphite supports.…”

Section: Introductionmentioning

confidence: 99%

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Molecular design driving tetraporphyrin self-assembly on graphite: a joint STM, electrochemical and computational study

et al. 2016

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Tuning the intermolecular interactions among suitably designed molecules forming highly ordered self-assembled monolayers is a viable approach to control their organization at the supramolecular level. Such a tuning is particularly important when applied to sophisticated molecules combining functional units which possess specific electronic properties, such as electron/energy transfer, in order to develop multifunctional systems. Here we have synthesized two tetraferrocene-porphyrin derivatives that by design can selectively self-assemble at the graphite/liquid interface into either face-on or edge-on monolayer-thick architectures. The former supramolecular arrangement consists of two-dimensional planar networks based on hydrogen bonding among adjacent molecules whereas the latter relies on columnar assembly generated through intermolecular van der Waals interactions. Scanning Tunneling Microscopy (STM) at the solid-liquid interface has been corroborated by cyclic voltammetry measurements and assessed by theoretical calculations to gain multiscale insight into the arrangement of the molecule with respect to the basal plane of the surface. The STM analysis allowed the visualization of these assemblies with a sub-nanometer resolution, and cyclic voltammetry measurements provided direct evidence of the interactions of porphyrin and ferrocene with the graphite surface and offered also insight into the dynamics within the face-on and edge-on assemblies. The experimental findings were supported by theoretical calculations to shed light on the electronic and other physical properties of both assemblies. The capability to engineer the functional nanopatterns through self-assembly of porphyrins containing ferrocene units is a key step toward the bottom-up construction of multifunctional molecular nanostructures and nanodevices.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular design driving tetraporphyrin self-assembly on graphite: a joint STM, electrochemical and computational study

et al. 2016

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“…The most common strategy to steer the formation of van der Waals driven layers is the use of molecules appropriately functionalized with alkyl chains. The van der Waals attraction between these chains leads to layers in which the chains interdigitate, as shown in Figure a. A surprising variety of structures can be formed in this way .…”

Section: Self‐assemblymentioning

confidence: 98%

Multi‐Component Organic Layers on Metal Substrates

et al. 2015

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Increasingly high hopes are being placed on organic semiconductors for a variety of applications. Progress along these lines, however, requires the design and growth of increasingly complex systems with well-defined structural and electronic properties. These issues have been studied and reviewed extensively in single-component layers, but the focus is gradually shifting towards more complex and functional multi-component assemblies such as donor-acceptor networks. These blends show different properties from those of the corresponding single-component layers, and the understanding on how these properties depend on the different supramolecular environment of multi-component assemblies is crucial for the advancement of organic devices. Here, our understanding of two-dimensional multi-component layers on solid substrates is reviewed. Regarding the structure, the driving forces behind the self-assembly of these systems are described. Regarding the electronic properties, recent insights into how these are affected as the molecule's supramolecular environment changes are explained. Key information for the design and controlled growth of complex, functional multicomponent structures by self-assembly is summarized.

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“…Designing and controlling the self‐assembled nanostructure on surface/interface has become increasingly important in the preparation of materials and devices in nanometer scale, which have potential applications from nanotechnology to fundamental surface science . There are many factors that influence the surface pattern, such as the molecular chemical structure and substrate . Additionally, the environmental factors (temperature, ratio, electric and magnetic field, light irradiation, time, PH, solvent, concentration, etc.)…”

Section: Introductionmentioning

confidence: 99%

Concentration induced the interfacial self‐assembly polymorphism of 4, 4′‐dihexadecyloxy‐benzophenon by scanning tunneling microscopy

Xie

Miao

2013

Surface & Interface Analysis

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The concentration effect on a two-dimensional (2D) self-assembly of 4, 4 0 -dihexadecyloxy-benzophenon (DHB) has been investigated by scanning tunneling microscopy. The self-assembly of DHB at the phenyloctane/graphite interface was concentration dependent. Under low concentration, the DHB molecules were adsorbed intactly on the graphite surface. With the increasing of concentration, one of side chains connecting the conjugated moiety stretched into the liquid phase. The coexistence of two self-assembled structures was observed in a moderate concentration. The result indicated that the van der Waals interactions between the molecules and the graphite lattice were decreasing with the increasing concentration. After the samples were placed in ambient conditions over 24 h, a different self-assembled structure was obtained on the gas/solid interface, in which the DHB molecules were adsorbed on the surface with only one of the side chains. Both the benzophenon core and the other side chain were extended to the gas phase. The results demonstrated that concentration played an important role in forming the 2D molecular self-assembly and provided an efficient approach for the control of the DHB molecular nanostructure.

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Chain‐length‐adjusted assembly of substituted porphyrins on graphite

Cited by 46 publications

References 22 publications

Molecular design driving tetraporphyrin self-assembly on graphite: a joint STM, electrochemical and computational study

Molecular design driving tetraporphyrin self-assembly on graphite: a joint STM, electrochemical and computational study

Multi‐Component Organic Layers on Metal Substrates

Concentration induced the interfacial self‐assembly polymorphism of 4, 4′‐dihexadecyloxy‐benzophenon by scanning tunneling microscopy

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