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. (2022). On-surface synthesis and characterization of nitrogen-substituted undecacenes. Nature Communications, 13(1), p. 511. Springer Nature 10.1038/s41467-022-27961-1
|
Text
22_Eimre_Nat._Commun._On-surface_synthesis_and_characterization_of_nitrogen-substituted_undecacenes.pdf - Published Version Available under License Creative Commons: Attribution (CC-BY). Download (4MB) | Preview |
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.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Fasel, Roman |
Subjects: |
500 Science > 530 Physics 500 Science > 540 Chemistry |
ISSN: |
2041-1723 |
Publisher: |
Springer Nature |
Language: |
English |
Submitter: |
Roman Fasel |
Date Deposited: |
25 Feb 2022 14:05 |
Last Modified: |
05 Dec 2022 16:07 |
Publisher DOI: |
10.1038/s41467-022-27961-1 |
PubMed ID: |
35082284 |
BORIS DOI: |
10.48350/165237 |
URI: |
https://boris.unibe.ch/id/eprint/165237 |
Actions (login required)
 |
Edit item |