Transferring axial molecular chirality through a sequence of on-surface reactions

Merino-Díez, Néstor; Mohammed, Mohammed S. G.; Castro‐Esteban, Jesús; Colazzo, Luciano; Berdonces‐Layunta, Alejandro; Lawrence, James; Pascual, José; Oteyza, Dimas G. de; Peña, Diego

doi:10.1039/d0sc01653e

Cited by 24 publications

(23 citation statements)

References 52 publications

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“…1 Conventional solution-phase dehydrogenative C aryl -C aryl couplings have recently been expanded to on-surface thermally-triggered cyclodehydrogenation reactions, 1,9,10 which allow precise assembly of rationally designed molecular precursors into a gamut of well-defined sp 2 -bonded graphitic nanoarchitectures, such as fullerenes, 11,12 nanographenes, 13,14 carbon nanotubes, 15 and graphene nanoribbons (GNRs). [16][17][18][19][20][21][22][23][24][25] In the latter case, the reported two-step approach 16 opens a new era for the synthesis of atomically precise GNRs of various topologies and sizes on noble metal surfaces. [20][21][22][23][24][26][27][28] A prominent case is the seven-carbon-wide armchair GNR (7-aGNR) made from 10,10'-dibromo-9,9'-bianthracene (DBBA) molecular precursors on Au(111) surface through dehalogenation/polymerization 29 followed by cyclodehydrogenation.…”

Section: Introductionmentioning

confidence: 98%

On-surface cyclodehydrogenation reaction pathway determined by selective molecular deuterations

Xiao

Bonnesen

et al. 2021

Chem. Sci.

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Section: Introductionmentioning

confidence: 98%

On-surface cyclodehydrogenation reaction pathway determined by selective molecular deuterations

Xiao

Bonnesen

et al. 2021

Chem. Sci.

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“…Here, we use bond-resolving scanning probe microscopy (BR-SPM), in combination with theoretical calculations, to study the effects of exposing narrow chiral GNRs [(3,1)-chGNRs] − synthesized under vacuum to ambient conditions, as well as to a low pressure of pure oxygen. As (3,1)-chGNRs consist of alternating zigzag and armchair segments, they are expected to be particularly vulnerable to oxidation, in particular at their zigzag edge sites.…”

Section: Introductionmentioning

confidence: 99%

Chemical Stability of (3,1)-Chiral Graphene Nanoribbons

et al. 2021

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Nanostructured graphene has been widely studied in recent years due to the tunability of its electronic properties and its associated interest for a variety of fields, such as nanoelectronics and spintronics. However, many of the graphene nanostructures of technological interest are synthesized under ultrahigh vacuum, and their limited stability as they are brought out of such an inert environment may compromise their applicability. In this study, a combination of bondresolving scanning probe microscopy (BR-SPM), along with theoretical calculations, has been employed to study (3,1)chiral graphene nanoribbons [(3,1)-chGNRs] that were synthesized on a Au(111) surface and then exposed to oxidizing environments. Exposure to the ambient atmosphere, along with the required annealing treatment to desorb a sufficiently large fraction of contaminants to allow for its postexposure analysis by BR-SPM, revealed a significant oxidation of the ribbons, with a dramatically disruptive effect on their electronic properties. More controlled experiments avoiding high temperatures and exposing the ribbons only to low pressures of pure oxygen show that also under these more gentle conditions the ribbons are oxidized. From these results, we obtain additional insights into the preferential reaction sites and the nature of the main defects that are caused by oxygen. We conclude that graphene nanoribbons with zigzag edge segments require forms of protection before they can be used in or transferred through ambient conditions.

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“…In a very recent publication, de Oteyza and co‐workers succeeded in transferring axial molecular chirality through a sequence of on‐surface reactions to prochiral graphene nanoribbons. [ 128 ] All these studies clearly show that a great number of small organic molecules can be potentially used as chiral sources for chiral modification of graphene family materials, and the resulting chiral hybrids are worthy to be continuously exploited for diverse applications. The substantial number of studies also evidence the significant importance of chiral graphene materials.…”

Section: Construction Of Chiral Graphene Hybrid Materialsmentioning

confidence: 99%

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

et al. 2021

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Chirality has become an important research subject. The research areas associated with chirality are under substantial development. Meanwhile, graphene is a rapidly growing star material and has hard‐wired into diverse disciplines. Rational combination of graphene and chirality undoubtedly creates unprecedented functional materials and may also lead to great findings. This hypothesis has been clearly justified by the sizable number of studies. Unfortunately, there has not been any previous review paper summarizing the scattered studies and advancements on this topic so far. This overview paper attempts to review the progress made in chiral materials developed from graphene and their derivatives, with the hope of providing a systemic knowledge about the construction of chiral graphenes and chiral applications thereof. Recently emerging directions, existing challenges, and future perspectives are also presented. It is hoped this paper will arouse more interest and promote further faster progress in these significant research areas.

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Transferring axial molecular chirality through a sequence of on-surface reactions

Abstract: The axial chirality of reactants is transferred through multistep on-surface reactions to chiral polymers and to prochiral graphene nanoribbons.

Cited by 24 publications

References 52 publications

On-surface cyclodehydrogenation reaction pathway determined by selective molecular deuterations

On-surface cyclodehydrogenation reaction pathway determined by selective molecular deuterations

Chemical Stability of (3,1)-Chiral Graphene Nanoribbons

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

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