Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Bald, Ilko; Wang, Yao-guang; Dong, Mingdong; Rosén, Christian; Ravnsbæk, Jens B.; Zhuang, Guilin; Gothelf, Kurt V.; Wang, Jianguo; Besenbacher, Flemming

doi:10.1002/smll.201002033

Cited by 22 publications

(19 citation statements)

References 50 publications

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“…The planarity mimicked the adsorption to the gold surfaces and the structure in the crystal. It was shown previously that gold surfaces had little interactions with the adsorbates, which justified our computational approach . Furthermore, the planar symmetry provided a clear σ–π separation, which was useful in our analysis.…”

Section: Computational Detailssupporting

confidence: 62%

Cooperativity in the Self‐Assembly of the Guanine Nucleobase into Quartet and Ribbon Structures on Surfaces

Paragi

Guerra

2017

Chemistry A European J

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The guanine nucleobase can self-assemble into tetrameric or ribbon structures on surfaces or in solution. The origin for the occurrence of different aggregation patterns has not yet been investigated. Herein, a quantum chemical study on the different self-assembled structures of guanine and xanthine by using dispersion-corrected DFT is presented. Theoretical investigations can be used to explain, from an electronic point of view, the differences between the experimental findings. With quantitative Kohn-Sham molecular orbital theory and the accompanying energy decomposition analysis, the hydrogen-bonding mechanism within the guanine ribbons can be disclosed and the preferred self-assembled structures under different experimental conditions can be explained. An important role of the σ-electronic system in the guanine self-assembled structures is revealed as the main factor for the switch between different arrangements on surfaces and in crystals.

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Section: Computational Detailssupporting

confidence: 62%

Cooperativity in the Self‐Assembly of the Guanine Nucleobase into Quartet and Ribbon Structures on Surfaces

Paragi

Guerra

2017

Chemistry A European J

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“…It is known that tiny alteration on the molecular structures may significantly change the intermolecular interactions and consequently subtly tune the supramolecular assembly. In previous work, Bald et al have investigated the effect of methylation on guanine assembly and concluded that a methyl group not only blocks specific H‐bonding sites but also alters the strength of the remaining hydrogen bonds . In our experiment, the substituent alkyl chain has similar effect on the intermolecular interactions of thymine head groups.…”

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confidence: 58%

Thymine and Adenine Tetrads Formed on Anisotropic Metal Surfaces

Zhong

Blömker

Mück‐Lichtenfeld

et al. 2013

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The interplay of the Au(110) surface and alkyl-substituted DNA bases induces reorganization of the surface with parallel atomic grooves, while the enhanced surface anisotropy constrains the substituent alkyl chains along the grooves. Every four molecules are bound together through H-bonds while further possible H-bonds are prohibited by either the alkyl chains or the groove borders, resulting in separated tetrad structures located in the grooves.

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“…Methylation of NB is an important control mechanism in biology which is applied, for example, in the regulation of gene expression . The effect of methylation on the intermolecular interactions between G molecules was recently studied by Wang and co‐workers . The STM analysis, corroborated by density functional theory (DFT), revealed that the methylation of guanine can have subtle effects on both the pairing nature and the strength of H‐bonds, with a strong dependence on the position of methylation.…”

Section: Self‐assembly In 2dmentioning

confidence: 99%

Self‐assembly of Natural and Unnatural Nucleobases at Surfaces and Interfaces

Ciesielski

Garah

Masiero

et al. 2015

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The self-assembly of small organic molecules interacting via non-covalent forces is a viable approach towards the construction of highly ordered nanostructured materials. Among various molecular components, natural and unnatural nucleobases can undergo non-covalent self-association to form supramolecular architectures with ad hoc structural motifs. Such structures, when decorated with appropriate electrically/optically active units, can be used as scaffolds to locate such units in pre-determined positions in 2D on a surface, thereby paving the way towards a wide range of applications, e.g., in optoelectronics. This review discusses some of the basic concepts of the supramolecular engineering of natural and unnatural nucleobases and derivatives thereof as well as self-assembly processes on conductive solid substrates, as investigated by scanning tunnelling microscopy in ultra-high vacuum and at the solid/liquid interface. By unravelling the structure and dynamics of these self-assembled architectures with a sub-nanometer resolution, a greater control over the formation of increasingly sophisticated functional systems is achieved. The ability to understand and predict how nucleobases interact, both among themselves as well as with other molecules, is extremely important, since it provides access to ever more complex DNA- and RNA-based nanostructures and nanomaterials as key components in nanomechanical devices.

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Control of Self‐Assembled 2D Nanostructures by Methylation of Guanine

Cited by 22 publications

References 50 publications

Cooperativity in the Self‐Assembly of the Guanine Nucleobase into Quartet and Ribbon Structures on Surfaces

Cooperativity in the Self‐Assembly of the Guanine Nucleobase into Quartet and Ribbon Structures on Surfaces

Thymine and Adenine Tetrads Formed on Anisotropic Metal Surfaces

Self‐assembly of Natural and Unnatural Nucleobases at Surfaces and Interfaces

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