Length-dependent symmetry in narrow chevron-like graphene nanoribbons

Houtsma, R. S. Koen; Enache, Mihaela; Havenith, Remco W. A.; Stöhr, Meike

doi:10.1039/d2na00297c

Cited by 2 publications

(4 citation statements)

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“…This molecule was previously studied on Au(111) and Cu(111). [27,28] On Au(111), DBCh forms a chiral, porous self-assembled network that may be transformed into chevron-like graphene nanoribbons upon annealing through stepwise Ullmann-type coupling and surface-assisted cyclodehydrogenation reactions.…”

Section: Introductionmentioning

confidence: 99%

“…This molecule was previously studied on Au(111) and Cu(111). [ 27,28 ] On Au(111), DBCh forms a chiral, porous self‐assembled network that may be transformed into chevron‐like graphene nanoribbons upon annealing through stepwise Ullmann‐type coupling and surface‐assisted cyclodehydrogenation reactions. On Cu(111), DBCh readily debrominates at room temperature, leading to the formation of chiral organometallic polymers which cannot be transformed into covalently bonded structures.…”

Section: Introductionmentioning

confidence: 99%

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On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Houtsma,

van Zuilen,

Stöhr

2023

Adv Materials Inter

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Ullmann‐type coupling is the most widely used on‐surface reaction to form rationally designed bottom‐up molecular nanoarchitectures. A commonly observed reaction product in this reaction is an organometallic phase, however little is known about the formation of this phase. The on‐surface polymerization of the prochiral precursor 6,12‐dibromochrysene (DBCh) on Ag(111) is studied. Upon annealing of DBCh on Ag(111), a linear organometallic polymer forms. However, the delicate energy balance involved in the polymerization of DBCh is such that, at room temperature, several reaction intermediates, which eventually lead to the formation of the organometallic polymer, can be observed experimentally. Organometallic monomers, dimers, and trimers are finds, that self‐assemble into distinct networks. The experimental availability of these reaction intermediates provides key insights into the formation of the organometallic polymer. Comparing the chirality of the intermediates and the polymer sheds additional light on the reaction mechanism leading to the formation of the polymer. The main finding is that the organometallic polymer is not formed by a simple coupling of the reaction intermediates, but rather requires the breaking and re‐establishing of the C─Ag bonds. Additionally, a Br‐enhanced growth mode is observed, where the split‐off halogens align the polymers, which results in an increased polymer length.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Houtsma,

van Zuilen,

Stöhr

2023

Adv Materials Inter

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“…4,5 Although the main steps of the synthesis for the covalent organic networks are common for many aryl halides, significant differences may arise in the kinetics and thermodynamics of the polymerization reaction on different coinage metals, such as Cu and Au. [6][7][8][9][10][11] As an example, the 1,3,6,8-tetrabromopyrene (Br 4 Py, see Fig. 1a for chemical structure) is completely debrominated on the Cu(111) surface already at room temperature, as shown by the X-ray photoelectron spectroscopy (XPS) measurements.…”

Section: Introductionmentioning

confidence: 99%

“…Although the main steps of the synthesis for the covalent organic networks are common for many aryl halides, significant differences may arise in the kinetics and thermodynamics of the polymerization reaction on different coinage metals, such as Cu and Au. 6–11…”

Section: Introductionmentioning

confidence: 99%

Theoretical insights into the interplay between metal–organic and covalent bonding in single-layer molecular networks formed by halogen dissociation

Ibenskas,

Šimėnas,

Tornau

2024

Phys. Chem. Chem. Phys.

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Length-dependent symmetry in narrow chevron-like graphene nanoribbons

Abstract: We report the structural and electronic properties of narrow chevron-like graphene nanoribbons (GNRs), which depending on their length are either mirror or inversion symmetric. Additionally, GNRs of different length can...

Cited by 2 publications

References 58 publications

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

On‐Surface Ullmann‐Type Coupling: Reaction Intermediates and Organometallic Polymer Growth

Theoretical insights into the interplay between metal–organic and covalent bonding in single-layer molecular networks formed by halogen dissociation

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