On-surface synthesis and characterization of nitrogen-substituted undecacenes

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

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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

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