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

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Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111) : The role of organometallic intermediates. / Simonov, K. A.; Generalov, A. V.; Vinogradov, A. S.; Svirskiy, G. I.; Cafolla, A. A.; McGuinness, C.; Taketsugu, T.; Lyalin, A.; Mårtensson, N.; Preobrajenski, A. B.

In: Scientific Reports, Vol. 8, No. 1, 3506, 01.12.2018.

Research output: Contribution to journal › Article › peer-review

Author

Simonov, K. A. ; Generalov, A. V. ; Vinogradov, A. S. ; Svirskiy, G. I. ; Cafolla, A. A. ; McGuinness, C. ; Taketsugu, T. ; Lyalin, A. ; Mårtensson, N. ; Preobrajenski, A. B. / Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111) : The role of organometallic intermediates. In: Scientific Reports. 2018 ; Vol. 8, No. 1.

BibTeX

@article{d5bcb7adcd004d1889c85456effbd6d4,

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

abstract = "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.",

keywords = "ON-SURFACE SYNTHESIS, BOTTOM-UP FABRICATION, BORON-NITRIDE NANOSHEET, REVEALS CHIRAL EDGES, CONFINED POLYMERIZATION, ULLMANN POLYMERIZATION, COVALENT NETWORKS, BUILDING-BLOCKS, SUBSTRATE, CU(111)",

author = "Simonov, {K. A.} and Generalov, {A. V.} and Vinogradov, {A. S.} and Svirskiy, {G. I.} and Cafolla, {A. A.} and C. McGuinness and T. Taketsugu and A. Lyalin and N. M{\aa}rtensson and Preobrajenski, {A. B.}",

note = "Funding Information: The authors are grateful for the financial support from the Swedish Research Council, the Swedish Energy Agency (STEM), the European Research Council under the European Union{\textquoteright}s Seventh Framework Program (FP7/2007–2013)/ERC grant agreement n° [321319], Knut and Alice Wallenberg Foundation, the St. Petersburg State University (Grant No. 11.38.638.2013), the Russian Foundation for Basic Research (Grant No. 15-02-06369), the Science Foundation of Ireland through the Principal Investigator grant SFI P.I.09/IN.1. AL and TT are grateful for support from the Japan Society for the Promotion of Science (JSPS KAKENHI Grants 15K05387 and 16KT0047), the FLAGSHIP2020 program supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, within the priority study 5 (Development of New Fundamental Technologies for High-Efficiency Energy Creation, Conversion/Storage and Use) and the MEXT program Development of Environmental Technology using Nanotechnology. The computations were partly performed at the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: {\textcopyright} 2018 The Author(s). Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "2018",

month = dec,

day = "1",

doi = "10.1038/s41598-018-21704-3",

language = "English",

volume = "8",

journal = "Scientific Reports",

issn = "2045-2322",

publisher = "Nature Publishing Group",

number = "1",

}

RIS

TY - JOUR

T1 - Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111)

T2 - The role of organometallic intermediates

AU - Simonov, K. A.

AU - Generalov, A. V.

AU - Vinogradov, A. S.

AU - Svirskiy, G. I.

AU - Cafolla, A. A.

AU - McGuinness, C.

AU - Taketsugu, T.

AU - Lyalin, A.

AU - Mårtensson, N.

AU - Preobrajenski, A. B.

N1 - Funding Information: The authors are grateful for the financial support from the Swedish Research Council, the Swedish Energy Agency (STEM), the European Research Council under the European Union’s Seventh Framework Program (FP7/2007–2013)/ERC grant agreement n° [321319], Knut and Alice Wallenberg Foundation, the St. Petersburg State University (Grant No. 11.38.638.2013), the Russian Foundation for Basic Research (Grant No. 15-02-06369), the Science Foundation of Ireland through the Principal Investigator grant SFI P.I.09/IN.1. AL and TT are grateful for support from the Japan Society for the Promotion of Science (JSPS KAKENHI Grants 15K05387 and 16KT0047), the FLAGSHIP2020 program supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, within the priority study 5 (Development of New Fundamental Technologies for High-Efficiency Energy Creation, Conversion/Storage and Use) and the MEXT program Development of Environmental Technology using Nanotechnology. The computations were partly performed at the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: © 2018 The Author(s). Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/12/1

Y1 - 2018/12/1

N2 - 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.

AB - 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.

KW - ON-SURFACE SYNTHESIS

KW - BOTTOM-UP FABRICATION

KW - BORON-NITRIDE NANOSHEET

KW - REVEALS CHIRAL EDGES

KW - CONFINED POLYMERIZATION

KW - ULLMANN POLYMERIZATION

KW - COVALENT NETWORKS

KW - BUILDING-BLOCKS

KW - SUBSTRATE

KW - CU(111)

UR - http://www.scopus.com/inward/record.url?scp=85042543772&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/synthesis-armchair-graphene-nanoribbons-1010dibromo99bianthracene-molecules-ag111-role-organometalli

U2 - 10.1038/s41598-018-21704-3

DO - 10.1038/s41598-018-21704-3

M3 - Article

C2 - 29472611

AN - SCOPUS:85042543772

VL - 8

JO - Scientific Reports

JF - Scientific Reports

SN - 2045-2322

IS - 1

M1 - 3506

ER -

ID: 36209935