Formation of Hypoxanthine Tetrad by Reaction with Sodium Chloride: From Planar to Stereo

Chen, Chong; Ding, Peng; Mura, Manuela; Chen, Yanghan; Sun, Yuxiu; Kantorovich, Lev; Gersen, Henkjan; Besenbacher, Flemming; Yu, Miao

doi:10.1002/ange.201808613

“…On‐surface synthesis has been demonstrated to be an effective route in manufacturing low‐dimensional COFs with atomic precision . Many important types of organic chemical reactions have been successfully applied on surfaces, for example, Ullmann reaction, Glaser coupling, cycloaddition, and others.…”

Section: Methodsmentioning

confidence: 99%

Graphene‐Like Covalent Organic Framework with a Wide Band Gap Synthesized On Surface via Stepwise Reactions

Shi

¹

,

Zhou

²

,

Li

³

et al. 2020

Self Cite

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Developing graphene‐like two‐dimensional materials naturally possessing a band gap has sparked enormous interest. Thanks to the inherent wide band gap and high mobility in the 2D plane, covalent organic frameworks containing triazine rings (t‐COFs) hold great promise in this regard, whilst the synthesis of single‐layer t‐COFs remains highly challenging. Herein, we present the fabrication of a well‐defined graphene‐like t‐COF on Au(111). Instead of single/multiple‐step single‐type reactions commonly applied for on‐surface synthesis, distinct stepwise on‐surface reactions, including alkynyl cyclotrimerization, C−O bond cleavage, and C−H bond activation, are triggered on demand, leading to product evolution in a controlled step‐by‐step manner. Aside from the precise control in sophisticated on‐surface synthesis, this work proposes a single‐atomic‐layer organic semiconductor with a wide band gap of 3.41 eV.

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“…A closer look into the molecular chain structure reveals that the Na-CN ionic bonding at the molecular joints exhibits diverse configurations, ranging from three-fold to four-fold geometry. 33,34 We found that the precise domain structure depends on molecular coverage. At low coverage, e.g.…”

mentioning

confidence: 94%

Metal-Organic Superlattices Induced by Long-Range Repulsive Interactions on a Metal Surface

Yang,

Lotze,

Franke

et al. 2021

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0

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Chains of Na atoms and dicyanovinyl-quinquethiophene (DCV5T-Me 2 ) molecules with ionic bonds form a superlattice on Au(111). Through a detailed analysis of the interchain distances obtained from scanning tunneling microscopy images at various molecular coverages, we found that the chain arrangement substantially deviates from a random distribution of noninteracting chains. Instead, the distribution of chain spacings provides evidence for the existence of an interchain long-range repulsive potential.Furthermore, the experimental results can be modeled by a repulsive potential with a 1/d distance dependence, characteristic of Coulomb interactions. Density functional theory calculations of free-standing molecular chains reveal a charge depletion at the periphery of the chains, which is attributed to the intrinsic polar property of the molecule and is responsible for the long-range repulsion.

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Graphene‐Like Covalent Organic Framework with a Wide Band Gap Synthesized On Surface via Stepwise Reactions

Shi

¹

,

Zhou

²

,

Li

³

et al. 2020

Angewandte Chemie

Self Cite

1

0

View full text Add to dashboard Cite

Developing graphene‐like two‐dimensional materials naturally possessing a band gap has sparked enormous interest. Thanks to the inherent wide band gap and high mobility in the 2D plane, covalent organic frameworks containing triazine rings (t‐COFs) hold great promise in this regard, whilst the synthesis of single‐layer t‐COFs remains highly challenging. Herein, we present the fabrication of a well‐defined graphene‐like t‐COF on Au(111). Instead of single/multiple‐step single‐type reactions commonly applied for on‐surface synthesis, distinct stepwise on‐surface reactions, including alkynyl cyclotrimerization, C−O bond cleavage, and C−H bond activation, are triggered on demand, leading to product evolution in a controlled step‐by‐step manner. Aside from the precise control in sophisticated on‐surface synthesis, this work proposes a single‐atomic‐layer organic semiconductor with a wide band gap of 3.41 eV.

show abstract

Formation of Hypoxanthine Tetrad by Reaction with Sodium Chloride: From Planar to Stereo

Cited by 5 publications

References 40 publications

Graphene‐Like Covalent Organic Framework with a Wide Band Gap Synthesized On Surface via Stepwise Reactions

Graphene‐Like Covalent Organic Framework with a Wide Band Gap Synthesized On Surface via Stepwise Reactions

Metal-Organic Superlattices Induced by Long-Range Repulsive Interactions on a Metal Surface

Graphene‐Like Covalent Organic Framework with a Wide Band Gap Synthesized On Surface via Stepwise Reactions

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