Journal Article

FZJ-2021-03370

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Kekulene: On-Surface Synthesis, Orbital Structure, and Aromatic Stabilization

Haags, A. (Corresponding author)FZJ* ; Reichmann, A. ; Fan, Q. ; Egger, L. ; Kirschner, H. ; Naumann, T. ; Werner, S. ; Vollgraff, T. ; Sundermeyer, J. ; Eschmann, L. ; Yang, X.FZJ* ; Brandstetter, D. ; Posseik, F.FZJ* ; Koller, G. ; Gottwald, A. ; Richter, M. ; Ramsey, M. G. ; Rohlfing, M. ; Puschnig, P. ; Gottfried, J. M. ; Soubatch, S.FZJ* ; Tautz, F. S.FZJ*

2020
Soc. Washington, DC

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Please use a persistent id in citations: http://hdl.handle.net/2128/28612  doi:10.1021/acsnano.0c06798

Abstract: We revisit the question of kekulene’s aromaticity by focusing on the electronic structure of its frontier orbitals as determined by angle-resolved photoemission spectroscopy. To this end, we have developed a specially designed precursor, 1,4,7(2,7)-triphenanthrenacyclononaphane-2,5,8-triene, which allows us to prepare sufficient quantities of kekulene of high purity directly on a Cu(111) surface, as confirmed by scanning tunneling microscopy. Supported by density functional calculations, we determine the orbital structure of kekulene’s highest occupied molecular orbital by photoemission tomography. In agreement with a recent aromaticity assessment of kekulene based solely on C–C bond lengths, we conclude that the π-conjugation of kekulene is better described by the Clar model rather than a superaromatic model. Thus, by exploiting the capabilities of photoemission tomography, we shed light on the question which consequences aromaticity holds for the frontier electronic structure of a π-conjugated molecule.

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Contributing Institute(s):

1. Quantum Nanoscience (PGI-3)
2. John von Neumann - Institut für Computing (NIC)

Research Program(s):

1. 5213 - Quantum Nanoscience (POF4-521) (POF4-521)
2. DFG project 396769409 - Grundlagen der Photoemissionstomographie (396769409)

Appears in the scientific report 2021

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Database coverage:
; ; ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; Essential Science Indicators ; IF >= 10 ; JCR ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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