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On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups
We demonstrate on-surface deprotection of methylenedioxy groups which yielded graphene nanoribbons (GNRs) with edges functionalized by hydroxy groups. While anthracene trimer precursors functionalized with hydroxy groups did not yield GNRs, it was found that hydroxy groups are first protected as met...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
RSC
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9642360/ https://www.ncbi.nlm.nih.gov/pubmed/36381511 http://dx.doi.org/10.1039/d2na00031h |
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author | Ohtomo, Manabu Hayashi, Hironobu Shiotari, Akitoshi Kawamura, Mayu Hayashi, Ryunosuke Jippo, Hideyuki Yamaguchi, Junichi Ohfuchi, Mari Aratani, Naoki Sugimoto, Yoshiaki Yamada, Hiroko Sato, Shintaro |
author_facet | Ohtomo, Manabu Hayashi, Hironobu Shiotari, Akitoshi Kawamura, Mayu Hayashi, Ryunosuke Jippo, Hideyuki Yamaguchi, Junichi Ohfuchi, Mari Aratani, Naoki Sugimoto, Yoshiaki Yamada, Hiroko Sato, Shintaro |
author_sort | Ohtomo, Manabu |
collection | PubMed |
description | We demonstrate on-surface deprotection of methylenedioxy groups which yielded graphene nanoribbons (GNRs) with edges functionalized by hydroxy groups. While anthracene trimer precursors functionalized with hydroxy groups did not yield GNRs, it was found that hydroxy groups are first protected as methylenedioxy groups and then deprotected during the cyclo-dehydrogenation process to form GNRs with hydroxy groups. The X-ray photoemission spectroscopy and non-contact atomic force microscopy studies revealed that ∼20% of the methylenedioxy turned into hydroxy groups, while the others were hydrogen-terminated. The first-principles density functional theory (DFT) study on the cyclo-dehydrogenation process was performed to investigate the deprotection mechanism, which indicates that hydrogen atoms emerging during the cyclo-dehydrogenation process trigger the deprotection of methylenedioxy groups. The scanning tunneling spectroscopy study and DFT revealed a significant charge transfer from hydroxy to the Au substrate, causing an interface dipole and the HOMO being closer to the Fermi level when compared with hydrogen-terminated GNR/Au(111). This result demonstrates on-surface deprotection and indicates a possible new route to obtain GNRs with desired edge functionalization, which can be a critical component for high-performance devices. |
format | Online Article Text |
id | pubmed-9642360 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | RSC |
record_format | MEDLINE/PubMed |
spelling | pubmed-96423602022-11-14 On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups Ohtomo, Manabu Hayashi, Hironobu Shiotari, Akitoshi Kawamura, Mayu Hayashi, Ryunosuke Jippo, Hideyuki Yamaguchi, Junichi Ohfuchi, Mari Aratani, Naoki Sugimoto, Yoshiaki Yamada, Hiroko Sato, Shintaro Nanoscale Adv Chemistry We demonstrate on-surface deprotection of methylenedioxy groups which yielded graphene nanoribbons (GNRs) with edges functionalized by hydroxy groups. While anthracene trimer precursors functionalized with hydroxy groups did not yield GNRs, it was found that hydroxy groups are first protected as methylenedioxy groups and then deprotected during the cyclo-dehydrogenation process to form GNRs with hydroxy groups. The X-ray photoemission spectroscopy and non-contact atomic force microscopy studies revealed that ∼20% of the methylenedioxy turned into hydroxy groups, while the others were hydrogen-terminated. The first-principles density functional theory (DFT) study on the cyclo-dehydrogenation process was performed to investigate the deprotection mechanism, which indicates that hydrogen atoms emerging during the cyclo-dehydrogenation process trigger the deprotection of methylenedioxy groups. The scanning tunneling spectroscopy study and DFT revealed a significant charge transfer from hydroxy to the Au substrate, causing an interface dipole and the HOMO being closer to the Fermi level when compared with hydrogen-terminated GNR/Au(111). This result demonstrates on-surface deprotection and indicates a possible new route to obtain GNRs with desired edge functionalization, which can be a critical component for high-performance devices. RSC 2022-10-27 /pmc/articles/PMC9642360/ /pubmed/36381511 http://dx.doi.org/10.1039/d2na00031h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Ohtomo, Manabu Hayashi, Hironobu Shiotari, Akitoshi Kawamura, Mayu Hayashi, Ryunosuke Jippo, Hideyuki Yamaguchi, Junichi Ohfuchi, Mari Aratani, Naoki Sugimoto, Yoshiaki Yamada, Hiroko Sato, Shintaro On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title | On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title_full | On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title_fullStr | On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title_full_unstemmed | On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title_short | On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
title_sort | on-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9642360/ https://www.ncbi.nlm.nih.gov/pubmed/36381511 http://dx.doi.org/10.1039/d2na00031h |
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