Thorsten G. Lohr¹, José I. Urgel^2,3, Kristjan Eimre², Junzhi Liu⁴, Marco Di Giovannantonio², Shantanu Mishra², Reinhard Berger¹, Pascal Ruffieux², Carlo A. Pignedoli^2*, Roman Fasel^2,5*, Xinliang Feng¹

1 Center for Advancing Electronics and Faculty of Chemistry and Food Chemistry, Technical University of Dresden, 01062 Dresden, Germany

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

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

4 Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, People’s Republic of China

5 Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland

* Corresponding authors emails: carlo.pignedoli@empa.ch, roman.fasel@empa.ch

DOI10.24435/materialscloud:y1-cr [version v1]

Publication date: Oct 14, 2020

How to cite this record

Thorsten G. Lohr, José I. Urgel, Kristjan Eimre, Junzhi Liu, Marco Di Giovannantonio, Shantanu Mishra, Reinhard Berger, Pascal Ruffieux, Carlo A. Pignedoli, Roman Fasel, Xinliang Feng, On-surface synthesis of non-benzenoid nanographenes by oxidative ring-closure and ring-rearrangement reactions, Materials Cloud Archive 2020.121 (2020), https://doi.org/10.24435/materialscloud:y1-cr

Description

In this record we provide data supporting our recent results discussed in the fabrication of non-benzenoid nanographenes. Nanographenes (NGs) have gained increasing attention due to their immense potential as tailor-made organic materials for nanoelectronics and spintronics. They exhibit a rich spectrum of physicochemical properties that can be tuned by controlling the size or the edge structure or by introducing structural defects in the honeycomb lattice. In the published manuscript we report the design and on-surface synthesis of NGs containing several odd-membered polycycles induced by a thermal procedure on Au(111). Our scanning tunneling microscopy, noncontact atomic force microscopy, and scanning tunneling spectroscopy measurements, complemented by computational investigations, describe the formation of two nonbenzenoid NGs (2A,B) containing four embedded azulene units in the polycyclic framework, via on-surface oxidative ring-closure reactions. Interestingly, we observe surface-catalyzed skeletal ring rearrangement reactions in the NGs, which lead to the formation of additional heptagonal rings as well as pentalene and as-indacene units in 2A,B, respectively. 2A,B on Au(111) both exhibit narrow experimental frontier electronic gaps of 0.96 and 0.85 eV, respectively, and Fermi level pinning of their HOMOs together with considerable electron transfer to the substrate. Ab initio calculations estimate moderate open-shell biradical characters for the NGs in the gas phase.

Materials Cloud sections using this data

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File name	Size	Description
ReadMe.yaml MD5md5:a0e6687af9d37e710cca57b395a8354e	2.3 KiB	ReadMe file in yaml format listing the files contained in the record
calculations_geo-opt-pdos-stm.aiida MD5md5:f2385227d2e1ae2ede9d3e2fddd0eada Open this AiiDA archive on renkulab.io (https://renkulab.io/)	345.4 MiB	Archive of calculation nodes for calculations performed with AiiDA
data.tgz MD5md5:31f3163cbe1b969c16de91c49bb4e603	566.6 MiB	Tar file containing all other data files

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External references

Keywords

nanographenes open shell MARVEL/DD3 SNSF CSCS Horizon 2020 DFG-NSFC ab initio simulations