Kristjan Eimre^1*, José I. Urgel^1,2*, Hironobu Hayashi³, Marco Di Giovannantonio^4,5, Pascal Ruffieux⁴, Shizuka Sato³, Satoru Otomo³, Yee Seng Chan³, Naoki Aratani³, Daniele Passerone⁴, Oliver Gröning⁴, Hiroko Yamada³, Roman Fasel^4,6, Carlo Antonio Pignedoli^4*

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), https://doi.org/10.24435/materialscloud:mc-kj

Description

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.

Materials Cloud sections using this data

Files

File name	Size	Description
n-undeca-ads-calcs.aiida MD5md5:73d917a4aac945bc5c1809ffb8c4f6df 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.
nh-pent-undeca-ads-geo-afm.aiida MD5md5:93a49bb82e629413623de071c286f0ce 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.
data.tgz MD5md5:bde69e5ef4476f2debcd234cc2c5ed67	126.1 MiB	Compressed archive containing the files of the record. See ReadMe.yaml for detailed descriptions.
ReadMe.yaml MD5md5:bfd1f7112435cc5c2b1506c78813d9e3	37.4 KiB	Readme file in yaml format detailing the contents of the record.

License

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External references

Keywords

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