Ullmann coupling reaction of aryl chlorides on Au(111) using dosed Cu as a catalyst and the programmed growth of 2D covalent organic frameworks

Shi, Ke Ji; Zhang, Xin; Chen, Shu; Li, Deng-Yuan; Wu, Xin; Liu, Pei Nian

doi:10.1039/c6cc03137d

Cited by 47 publications

(40 citation statements)

References 39 publications

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“…Solid-vapor interface synthesis is often used by combination with ultrahigh vacuum (UHV) method [ 107 , 136 , 137 , 138 , 139 , 140 , 180 , 181 ]. Halogenate monomers will be turned into vapor at first and deposited on the surface of clean metal surface under ultrahigh vacuum.…”

Section: Developments Of Cofsmentioning

confidence: 99%

Covalent Organic Frameworks: From Materials Design to Biomedical Application

et al. 2017

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Covalent organic frameworks (COFs) are newly emerged crystalline porous polymers with well-defined skeletons and nanopores mainly consisted of light-weight elements (H, B, C, N and O) linked by dynamic covalent bonds. Compared with conventional materials, COFs possess some unique and attractive features, such as large surface area, pre-designable pore geometry, excellent crystallinity, inherent adaptability and high flexibility in structural and functional design, thus exhibiting great potential for various applications. Especially, their large surface area and tunable porosity and π conjugation with unique photoelectric properties will enable COFs to serve as a promising platform for drug delivery, bioimaging, biosensing and theranostic applications. In this review, we trace the evolution of COFs in terms of linkages and highlight the important issues on synthetic method, structural design, morphological control and functionalization. And then we summarize the recent advances of COFs in the biomedical and pharmaceutical sectors and conclude with a discussion of the challenges and opportunities of COFs for biomedical purposes. Although currently still at its infancy stage, COFs as an innovative source have paved a new way to meet future challenges in human healthcare and disease theranostic.

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Section: Developments Of Cofsmentioning

confidence: 99%

Covalent Organic Frameworks: From Materials Design to Biomedical Application

et al. 2017

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“…46 The result was rationalized by the fact that the C–Cl bond is stronger than the C–Br bond. 47−49 As a consequence, for DCBA, the dehalogenation temperature is elevated relative to that for DBBA and is higher than the cyclodehydrogenation temperature. This leads to a reversed reaction sequence, with cyclodehydrogenation preceding covalent coupling.…”

Section: Introductionmentioning

confidence: 99%

“…The exact sequence of thermally induced transformations is an interplay between the precursor molecule of interest and the metal substrate, and can additionally be affected by coadsorbed species. 49−51 Understanding what product is obtained therefore requires an understanding of the various elementary reaction steps and their activation temperatures. Although scanning tunneling microscopy (STM) and noncontact atomic force microscopy (nc-AFM) imaging allow the identification of reaction products and intermediates, these techniques lack the ability to monitor chemical transformations at annealing temperatures.…”

Section: Introductionmentioning

confidence: 99%

One Precursor but Two Types of Graphene Nanoribbons: On-Surface Transformations of 10,10′-Dichloro-9,9′-bianthryl on Ag(111)

et al. 2019

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On-surface synthesis has emerged in the last decade as a method to create graphene nanoribbons (GNRs) with atomic precision. The underlying premise of this bottom-up strategy is that precursor molecules undergo a well-defined sequence of inter- and intramolecular reactions, leading to the formation of a single product. As such, the structure of the GNR is encoded in the precursors. However, recent examples have shown that not only the molecule, but also the coinage metal surface on which the reaction takes place, plays a decisive role in dictating the nanoribbon structure. In this work, we use scanning probe microscopy and X-ray photoelectron spectroscopy to investigate the behavior of 10,10′-dichloro-9,9′-bianthryl (DCBA) on Ag(111). Our study shows that Ag(111) can induce the formation of both seven-atom wide armchair GNRs (7-acGNRs) and 3,1-chiral GNRs (3,1-cGNRs), demonstrating that a single molecule on a single surface can react to different nanoribbon products. We additionally show that coadsorbed dibromoperylene can promote surface-assisted dehydrogenative coupling in DCBA, leading to the exclusive formation of 3,1-cGNRs.

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“…A large variety of surface‐supported 2D networks were fabricated in ultrahigh vacuum (UHV) environment or at the liquid‐solid interface . In the latter case thermodynamic equilibrium conditions can be reached and extended well‐ordered networks can be formed.…”

Section: Figurementioning

confidence: 99%

“…Further annealing up to 510 °C allowed to improve the network quality and the PH score raised to 0.30 (Figure c). The same honeycomb network could be obtained using a sequential coupling strategy with a precursor bearing two different halogen types (4,4′′‐dichloro‐1,1′ : 4′,1′′‐terphenyl, DCTP, Figure d) . The low quality network obtained on Au(111) with the help of codeposited Cu adatom catalysts delivered a PH score of 0.16 (Figure e).…”

Section: Figurementioning

confidence: 99%

Persistent Homology to Quantify the Quality of Surface‐Supported Covalent Networks

2019

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Covalent networks formed by on-surface synthesis usually suffer from the presence of a large number of defects. We report on a methodology to characterize such two-dimensional networks from their experimental images obtained by scanning probe microscopy. The computation is based on a persistent homology approach and provides a quantitative score indicative of the network homogeneity. We compare our scoring method with results previously obtained using minimal spanning tree analyses and we apply it to some molecular systems appearing in the existing literature.[a] A.

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Ullmann coupling reaction of aryl chlorides on Au(111) using dosed Cu as a catalyst and the programmed growth of 2D covalent organic frameworks

Cited by 47 publications

References 39 publications

Covalent Organic Frameworks: From Materials Design to Biomedical Application

Covalent Organic Frameworks: From Materials Design to Biomedical Application

One Precursor but Two Types of Graphene Nanoribbons: On-Surface Transformations of 10,10′-Dichloro-9,9′-bianthryl on Ag(111)

Persistent Homology to Quantify the Quality of Surface‐Supported Covalent Networks

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