Evidence map›Paper›PMID 33186031›Full record

ArticleACS nano2020

Kekulene: On-Surface Synthesis, Orbital Structure, and Aromatic Stabilization.

Anja Haags, Alexander Reichmann, Qitang Fan, Larissa Egger, Hans Kirschner, Tim Naumann, Simon Werner, Tobias Vollgraff, Jörg Sundermeyer, Lukas Eschmann and 12 more

Open access · hybridAbstract read
In one paragraph

Article in ACS nano, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.

0numbers the graph read from it
0cells of the map it votes in
13citing papers in PubMed
2.5field-weighted citation impact, top 11% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

13 citing papers in PubMed, 48 citations in OpenAlex.

  1. Article
  2. Article
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  4. When Aromaticity Falls Short in Molecule-Surface Interactions.The journal of physical chemistry. C, Nanomaterials and interfaces · 2025
    Article
  5. Highly Structure-Selective On-Surface Synthesis of Isokekulene Versus Kekulene.Angewandte Chemie (International ed. in English) · 2025
    Article
  6. Article
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  11. Demonstrating the Impact of the Adsorbate Orientation on the Charge Transfer at Organic-Metal Interfaces.The journal of physical chemistry. C, Nanomaterials and interfaces · 2021
    Article
  12. Going beyond Pentacene: Photoemission Tomography of a Heptacene Monolayer on Ag(110).The journal of physical chemistry. C, Nanomaterials and interfaces · 2021
    Article
  13. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

22 authors at 5 institutions in 2 countries.

Anja HaagsPeter Grünberg Institut (PGI-3), Forschungszentrum Jülich, 52425 Jülich, Germany.
Alexander ReichmannInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.
Qitang FanFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.
Larissa EggerInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.
Hans KirschnerPhysikalisch-Technische Bundesanstalt (PTB), 10587 Berlin, Germany.
Tim NaumannFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.
Simon WernerFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.
Tobias VollgraffFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.
Jörg SundermeyerFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.
Lukas EschmannInstitut für Festkörpertheorie, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany.
Xiaosheng YangPeter Grünberg Institut (PGI-3), Forschungszentrum Jülich, 52425 Jülich, Germany.ORCID http://orcid.org/0000-0002-7632-0401
Dominik BrandstetterInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.
François C BocquetPeter Grünberg Institut (PGI-3), Forschungszentrum Jülich, 52425 Jülich, Germany.
Georg KollerInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.ORCID http://orcid.org/0000-0001-7741-2394
Alexander GottwaldPhysikalisch-Technische Bundesanstalt (PTB), 10587 Berlin, Germany.
Mathias RichterPhysikalisch-Technische Bundesanstalt (PTB), 10587 Berlin, Germany.
Michael G RamseyInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.
Michael RohlfingInstitut für Festkörpertheorie, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany.
Peter PuschnigInstitut für Physik, Karl-Franzens-Universität Graz, NAWI Graz, 8010 Graz, Austria.ORCID http://orcid.org/0000-0002-8057-7795
J Michael GottfriedFachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032 Marburg, Germany.ORCID http://orcid.org/0000-0001-5579-2568
Serguei SoubatchPeter Grünberg Institut (PGI-3), Forschungszentrum Jülich, 52425 Jülich, Germany.ORCID http://orcid.org/0000-0002-1455-0260
F Stefan TautzPeter Grünberg Institut (PGI-3), Forschungszentrum Jülich, 52425 Jülich, Germany.
Philipps University of Marburg · DEUniversity of Graz · ATForschungszentrum Jülich · DEPhysikalisch-Technische Bundesanstalt · DEUniversity of Münster · DE

Funding

Austrian Science Fund FWF I 3731Austrian Science Fund FWF P 27427Austrian Science Fund FWF P 27649
6 · The paper itself

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.

Indexed as

aromaticityARPESDFTkekulenephotoemissionSTM

Identifiers

PMID33186031
PMCPMC7690051
OpenAlexW3106016418

What OpenQuestion holds

Textmetadata
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.