On-surface synthesis and characterization of nitrogen-substituted undecacenes

Kristjan Eimre (), José I. Urgel (), Hironobu Hayashi, Marco Giovannantonio, Pascal Ruffieux, Shizuka Sato, Satoru Otomo, Yee Seng Chan, Naoki Aratani, Daniele Passerone, Oliver Gröning, Hiroko Yamada (), Roman Fasel () and Carlo A. Pignedoli ()
Additional contact information
Kristjan Eimre: Empa, Swiss Federal Laboratories for Materials Science and Technology
José I. Urgel: Empa, Swiss Federal Laboratories for Materials Science and Technology
Hironobu Hayashi: Nara Institute of Science and Technology (NAIST)
Marco Giovannantonio: Empa, Swiss Federal Laboratories for Materials Science and Technology
Pascal Ruffieux: Empa, Swiss Federal Laboratories for Materials Science and Technology
Shizuka Sato: Nara Institute of Science and Technology (NAIST)
Satoru Otomo: Nara Institute of Science and Technology (NAIST)
Yee Seng Chan: Nara Institute of Science and Technology (NAIST)
Naoki Aratani: Nara Institute of Science and Technology (NAIST)
Daniele Passerone: Empa, Swiss Federal Laboratories for Materials Science and Technology
Oliver Gröning: Empa, Swiss Federal Laboratories for Materials Science and Technology
Hiroko Yamada: Nara Institute of Science and Technology (NAIST)
Roman Fasel: Empa, Swiss Federal Laboratories for Materials Science and Technology
Carlo A. Pignedoli: Empa, Swiss Federal Laboratories for Materials Science and Technology

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract 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.

Date: 2022
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DOI: 10.1038/s41467-022-27961-1

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