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 deb...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2018-02-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-018-21704-3 |
| _version_ | 1818749372874096640 |
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| author | K. A. Simonov A. V. Generalov A. S. Vinogradov G. I. Svirskiy A. A. Cafolla C. McGuinness T. Taketsugu A. Lyalin N. Mårtensson A. B. Preobrajenski |
| author_facet | K. A. Simonov A. V. Generalov A. S. Vinogradov G. I. Svirskiy A. A. Cafolla C. McGuinness T. Taketsugu A. Lyalin N. Mårtensson A. B. Preobrajenski |
| author_sort | K. A. Simonov |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-18T04:02:44Z |
| format | Article |
| id | doaj.art-2d721c46f6824e65b8fb648d4903fd47 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-12-18T04:02:44Z |
| publishDate | 2018-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-2d721c46f6824e65b8fb648d4903fd472022-12-21T21:21:39ZengNature PortfolioScientific Reports2045-23222018-02-018111210.1038/s41598-018-21704-3Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediatesK. A. Simonov0A. V. Generalov1A. S. Vinogradov2G. I. Svirskiy3A. A. Cafolla4C. McGuinness5T. Taketsugu6A. Lyalin7N. Mårtensson8A. B. Preobrajenski9Department of Physics and Astronomy, Uppsala UniversityMAX IV Laboratory, Lund UniversityV.A. Fock Institute of Physics, St. Petersburg State UniversityV.A. Fock Institute of Physics, St. Petersburg State UniversitySchool of Physical Sciences, Dublin City UniversitySchool of Physics, Trinity College Dublin, College GreenDepartment of Chemistry, Faculty of Science, Hokkaido UniversityGlobal Research Center for Environment and Energy Based on Nanomaterials Science (GREEN), National Institute for Materials Science (NIMS)Department of Physics and Astronomy, Uppsala UniversityMAX IV Laboratory, Lund UniversityAbstract 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.https://doi.org/10.1038/s41598-018-21704-3 |
| spellingShingle | K. A. Simonov A. V. Generalov A. S. Vinogradov G. I. Svirskiy A. A. Cafolla C. McGuinness T. Taketsugu A. Lyalin N. Mårtensson A. B. Preobrajenski Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates Scientific Reports |
| title | Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates |
| title_full | Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates |
| title_fullStr | Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates |
| title_full_unstemmed | Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates |
| title_short | Synthesis of armchair graphene nanoribbons from the 10,10′-dibromo-9,9′-bianthracene molecules on Ag(111): the role of organometallic intermediates |
| title_sort | synthesis of armchair graphene nanoribbons from the 10 10 dibromo 9 9 bianthracene molecules on ag 111 the role of organometallic intermediates |
| url | https://doi.org/10.1038/s41598-018-21704-3 |
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