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On-surface synthesis and characterization of nitrogen-substituted undecacenes
Heteroatom substitution in acenes allows tailoring of their remarkable electronic properties, expected to include spin-polarization and magnetism for larger members of the acene family. Here, we present a strategy for the on-surface synthesis of three undecacene analogs substituted with four nitroge...
Autores principales: | , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8791976/ https://www.ncbi.nlm.nih.gov/pubmed/35082284 http://dx.doi.org/10.1038/s41467-022-27961-1 |
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author | Eimre, Kristjan Urgel, José I. Hayashi, Hironobu Di Giovannantonio, Marco Ruffieux, Pascal Sato, Shizuka Otomo, Satoru Chan, Yee Seng Aratani, Naoki Passerone, Daniele Gröning, Oliver Yamada, Hiroko Fasel, Roman Pignedoli, Carlo A. |
author_facet | Eimre, Kristjan Urgel, José I. Hayashi, Hironobu Di Giovannantonio, Marco Ruffieux, Pascal Sato, Shizuka Otomo, Satoru Chan, Yee Seng Aratani, Naoki Passerone, Daniele Gröning, Oliver Yamada, Hiroko Fasel, Roman Pignedoli, Carlo A. |
author_sort | Eimre, Kristjan |
collection | PubMed |
description | Heteroatom substitution in acenes allows tailoring of their remarkable electronic properties, expected to include spin-polarization and magnetism for larger members of the acene family. Here, we present a strategy for the on-surface synthesis of three undecacene analogs substituted with four nitrogen atoms on an Au(111) substrate, by employing specifically designed diethano-bridged precursors. A similarly designed precursor is used to synthesize the pristine undecacene molecule. By comparing experimental features of scanning probe microscopy with ab initio simulations, we demonstrate that the ground state of the synthesized tetraazaundecacene has considerable open-shell character on Au(111). Additionally, we demonstrate that the electronegative nitrogen atoms induce a considerable shift in energy level alignment compared to the pristine undecacene, and that the introduction of hydro-aza groups causes local anti-aromaticity in the synthesized compounds. Our work provides access to the precise fabrication of nitrogen-substituted acenes and their analogs, potential building-blocks of organic electronics and spintronics, and a rich playground to explore π-electron correlation. |
format | Online Article Text |
id | pubmed-8791976 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-87919762022-02-07 On-surface synthesis and characterization of nitrogen-substituted undecacenes Eimre, Kristjan Urgel, José I. Hayashi, Hironobu Di Giovannantonio, Marco Ruffieux, Pascal Sato, Shizuka Otomo, Satoru Chan, Yee Seng Aratani, Naoki Passerone, Daniele Gröning, Oliver Yamada, Hiroko Fasel, Roman Pignedoli, Carlo A. Nat Commun Article Heteroatom substitution in acenes allows tailoring of their remarkable electronic properties, expected to include spin-polarization and magnetism for larger members of the acene family. Here, we present a strategy for the on-surface synthesis of three undecacene analogs substituted with four nitrogen atoms on an Au(111) substrate, by employing specifically designed diethano-bridged precursors. A similarly designed precursor is used to synthesize the pristine undecacene molecule. By comparing experimental features of scanning probe microscopy with ab initio simulations, we demonstrate that the ground state of the synthesized tetraazaundecacene has considerable open-shell character on Au(111). Additionally, we demonstrate that the electronegative nitrogen atoms induce a considerable shift in energy level alignment compared to the pristine undecacene, and that the introduction of hydro-aza groups causes local anti-aromaticity in the synthesized compounds. Our work provides access to the precise fabrication of nitrogen-substituted acenes and their analogs, potential building-blocks of organic electronics and spintronics, and a rich playground to explore π-electron correlation. Nature Publishing Group UK 2022-01-26 /pmc/articles/PMC8791976/ /pubmed/35082284 http://dx.doi.org/10.1038/s41467-022-27961-1 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Eimre, Kristjan Urgel, José I. Hayashi, Hironobu Di Giovannantonio, Marco Ruffieux, Pascal Sato, Shizuka Otomo, Satoru Chan, Yee Seng Aratani, Naoki Passerone, Daniele Gröning, Oliver Yamada, Hiroko Fasel, Roman Pignedoli, Carlo A. On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title | On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title_full | On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title_fullStr | On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title_full_unstemmed | On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title_short | On-surface synthesis and characterization of nitrogen-substituted undecacenes |
title_sort | on-surface synthesis and characterization of nitrogen-substituted undecacenes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8791976/ https://www.ncbi.nlm.nih.gov/pubmed/35082284 http://dx.doi.org/10.1038/s41467-022-27961-1 |
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