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On-surface synthesis and characterization of nitrogen-substituted undecacenes

Kristjan Eimre1*, José I. Urgel1,2*, Hironobu Hayashi3, Marco Di Giovannantonio4,5, Pascal Ruffieux4, Shizuka Sato3, Satoru Otomo3, Yee Seng Chan3, Naoki Aratani3, Daniele Passerone4, Oliver Gröning4, Hiroko Yamada3, Roman Fasel4,6, Carlo Antonio Pignedoli4*

1 Empa - Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland

2 IMDEA Nanoscience, C/ Faraday 9, Campus de Cantoblanco, 28049 Madrid, Spain

3 Division of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, 630-0192, Japan

4 Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland

5 Istituto di Struttura della Materia-CNR (ISM-CNR), via Fosso del Cavaliere 100, 00133 Roma, Italy

6 Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland

* Corresponding authors emails: kristjan.eimre@empa.ch, jose-ignacio.urgel@imdea.org, carlo.pignedoli@empa.ch
DOI10.24435/materialscloud:mc-kj [version v1]

Publication date: Jan 11, 2022

How to cite this record

Kristjan Eimre, José I. Urgel, Hironobu Hayashi, Marco Di Giovannantonio, Pascal Ruffieux, Shizuka Sato, Satoru Otomo, Yee Seng Chan, Naoki Aratani, Daniele Passerone, Oliver Gröning, Hiroko Yamada, Roman Fasel, Carlo Antonio Pignedoli, On-surface synthesis and characterization of nitrogen-substituted undecacenes, Materials Cloud Archive 2022.2 (2022), doi: 10.24435/materialscloud:mc-kj.


In this record, we provide the data supporting our recent results on the synthesis of nitrogen-substituted undecacene analogs. Heteroatom substitution in acenes allows to tailor 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. In the publication where the results are discussed, the experimental features of scanning probe microscopy are compared with ab initio simulations, to demonstrate that the ground state of the synthesized tetraazaundecacene has considerable open-shell character on Au(111). Additionally, we demonstrate that 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 acene and its analogs, potential building-blocks of organic electronics and spintronics, and a rich playground to explore pi-electron correlation.

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File name Size Description
Open this AiiDA archive on renkulab.io (https://renkulab.io/)
363.7 MiB Archive of AiiDA nodes for the adsorption configuration and scanning probe calculations for all systems except the pentagon-containing analog.
Open this AiiDA archive on renkulab.io (https://renkulab.io/)
93.4 MiB Archive of AiiDA nodes for the adsorption configuration and scanning probe calculations for the pentagon-containing system.
126.1 MiB Compressed archive containing the files of the record. See ReadMe.yaml for detailed descriptions.
37.4 KiB Readme file in yaml format detailing the contents of the record.


Files and data are licensed under the terms of the following license: Creative Commons Attribution 4.0 International.
Metadata, except for email addresses, are licensed under the Creative Commons Attribution Share-Alike 4.0 International license.

External references

Journal reference (Manuscript, where the results are discussed.)
K. Eimre, J. I. Urgel, H. Hayashi, M. Di Giovannantonio, P. Ruffieux, S. Sato, S. Otomo, Y. S. Chan, N. Aratani, D. Passerone, O. Gröning, H. Yamada, R. Fasel, C. A. Pignedoli Nat. Commun. (2022) doi:10.1038/s41467-022-27961-1


heteroacenes on surface synthesis open-shell aromaticity experimental SNSF MARVEL/DD3 CSCS

Version history:

2022.2 (version v1) [This version] Jan 11, 2022 DOI10.24435/materialscloud:mc-kj