Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

Bronner, Christopher; Marangoni, Tomas; Rizzo, Daniel J.; Durr, Rebecca A.; Jørgensen, Jakob Holm; Fischer, Felix R.; Crommie, Michael F.

doi:10.1021/acs.jpcc.7b02896

Cited by 36 publications

(47 citation statements)

References 58 publications

(155 reference statements)

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“…The doped chGNRs, as the pristine ones, display preferential orientations on the substrate, but notably shorter than pristine chGNRs [21,24], reaching lengths of up to 15 nm. We speculate that the attachment of NH 2 groups lowers the diffusion of precursors and thus hinders their polymerization processes [44]. The edges of the resulting NH 2 -chGNRs are quite inhomogeneous, and their width is larger than pristine chGNRs, suggesting the presence of a certain amount of NH 2 groups attached to the edges (see Supporting Information).…”

Section: Resultsmentioning

confidence: 97%

Band Depopulation of Graphene Nanoribbons Induced by Chemical Gating with Amino Groups

Brandimarte

Vilas‐Varela

et al. 2020

ACS Nano

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The electronic properties of graphene nanoribbons (GNRs) can be precisely tuned by chemical doping. Here we demonstrate that amino (NH 2 ) functional groups attached at the edges of chiral GNRs (chGNRs) can efficiently gate the chGNRs and lead to the valence band (VB) depopulation on a metallic surface. The NH 2 -doped chGNRs are grown by onsurface synthesis on Au(111) using functionalized bianthracene precursors. Scanning tunneling spectroscopy resolves that the NH 2 groups significantly upshift the bands of chGNRs, causing the Fermi level crossing of the VB onset of chGNRs. Through density functional theory simulations we confirm that the holedoping behavior is due to an upward shift of the bands induced by the edge NH 2 groups.

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Section: Resultsmentioning

confidence: 97%

Band Depopulation of Graphene Nanoribbons Induced by Chemical Gating with Amino Groups

Brandimarte

Vilas‐Varela

et al. 2020

ACS Nano

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“…The critical role of diffusion for the formation of GNRs was recently demonstrated by C. Bronner et al . in their study of iodine- and bromine- containing molecules on the Au(111) surface 38 . It was shown that even though dehalogenation of iodinated monomers occurs on gold at lower temperature, the surface-stabilized monomers do not start polymerisation right away due to their reduced diffusivity.…”

Section: Discussionmentioning

confidence: 99%

“…Being part of a multistep process, the Ullmann-type reaction between specifically designed molecules is aimed to result in the formation of polymerized molecular chains, which can be transformed to atomically precise graphene nanoribbons upon further cyclodehydrogenation at higher temperatures 7 , 15 . In the majority of the studies this method was used for the preparation of GNRs with various atomic structures on Au(111), Au(110) or Au(788) substrates 7 , 15 – 29 , 38 . In particular, the most widely studied nanoribbon is that with armchair edges and a width (N) of seven carbon atoms (7-AGNR) that grows from the 10,10′-dibromo-9,9′-bianthracene (DBBA) 15 – 20 , 23 , 25 , 29 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates

Simonov

Generalov

Виноградов

et al. 2018

Sci Rep

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We investigate the bottom-up growth of N = 7 armchair graphene nanoribbons (7-AGNRs) from the 10,10′-dibromo-9,9′-bianthracene (DBBA) molecules on Ag(111) with the focus on the role of the organometallic (OM) intermediates. It is demonstrated that DBBA molecules on Ag(111) are partially debrominated at room temperature and lose all bromine atoms at elevated temperatures. Similar to DBBA on Cu(111), debrominated molecules form OM chains on Ag(111). Nevertheless, in contrast with the Cu(111) substrate, formation of polyanthracene chains from OM intermediates via an Ullmann-type reaction is feasible on Ag(111). Cleavage of C–Ag bonds occurs before the thermal threshold for the surface-catalyzed activation of C–H bonds on Ag(111) is reached, while on Cu(111) activation of C–H bonds occurs in parallel with the cleavage of the stronger C–Cu bonds. Consequently, while OM intermediates obstruct the Ullmann reaction between DBBA molecules on the Cu(111) substrate, they are required for the formation of polyanthracene chains on Ag(111). If the Ullmann-type reaction on Ag(111) is inhibited, heating of the OM chains produces nanographenes instead. Heating of the polyanthracene chains produces 7-AGNRs, while heating of nanographenes causes the formation of the disordered structures with the possible admixture of short GNRs.

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“…By functionalizing one of those groups or a combination thereof can implement heteroatom‐doped GNRs, phenyl‐modified CGNRs, and so forth. Besides, iodinated precursors instead of the brominated ones can also be applied to form GNRs . Therefore, the DBTT‐typed precursors play an important role in the preparation of pristine, doped CGNRs, and even heterojunctions.…”

Section: Crucial Elements and Growth Procedures Of Gnrsmentioning

confidence: 99%

Modified Engineering of Graphene Nanoribbons Prepared via On‐Surface Synthesis

Zhou

2019

Advanced Materials

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1D graphene nanoribbons (GNRs) have a bright future in the fabrication of next‐generation nanodevices because of their nontrivial electronic properties and tunable bandgaps. To promote the application of GNRs, preparation strategies of miscellaneous GNRs have to be developed. The GNRs prepared by top‐down approaches are accompanied by uncontrolled edges and structures. In order to overcome the difficulties, bottom‐up methods are widely used in the growth of various GNRs due to controllability of GNRs' features. Among those bottom‐up methods, the on‐surface synthesis is a promising approach to prepare GNRs with distinct widths, edge/backbone structures, and so forth. Therefore, modified engineering of the GNRs prepared via on‐surface synthesis is of great significance in controllable preparation of GNRs and their potential applications. In the past decade, there have been a lot of reports on controllable preparation of GNRs using on‐surface synthesis approach. Herein, the advances of GNRs grown via on‐surface growth strategy are described. Several growth parameters, the latest advances in the modification of the GNR structure and width, the GNR doping/co‐doping with heteroatoms, a variety of GNR heterojunctions, and the device application of GNRs are reviewed. Finally, the opportunities and challenges are discussed.

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Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

Cited by 36 publications

References 58 publications

Band Depopulation of Graphene Nanoribbons Induced by Chemical Gating with Amino Groups

Band Depopulation of Graphene Nanoribbons Induced by Chemical Gating with Amino Groups

Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates

Modified Engineering of Graphene Nanoribbons Prepared via On‐Surface Synthesis

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