Evidence map›Paper›PMID 38429274›Full record

ArticleNature communications2024

On-surface cyclization of vinyl groups on poly-para-phenylene involving an unusual pentagon to hexagon transformation.

Marco Di Giovannantonio, Zijie Qiu, Carlo A Pignedoli, Sobi Asako, Pascal Ruffieux, Klaus Müllen, Akimitsu Narita, Roman Fasel

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
1.1field-weighted citation impact, top 26% 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

4 citing papers in PubMed, 6 citations in OpenAlex.

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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

8 authors at 6 institutions in 5 countries.

Marco Di Giovannantonio *Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600, Dübendorf, Switzerland. marco.digiovannantonio@ism.cnr.it.ORCID http://orcid.org/0000-0001-8658-9183
Zijie Qiu *Max Planck Institute for Polymer Research, 55128, Mainz, Germany.ORCID http://orcid.org/0000-0003-0728-1178
Carlo A Pignedoli *Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600, Dübendorf, Switzerland.ORCID http://orcid.org/0000-0002-8273-6390
Sobi AsakoRIKEN Center for Sustainable Resource Science, Wako, Saitama, 351-0198, Japan.ORCID http://orcid.org/0000-0003-4525-5317
Pascal RuffieuxEmpa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600, Dübendorf, Switzerland.ORCID http://orcid.org/0000-0001-5729-5354
Klaus MüllenMax Planck Institute for Polymer Research, 55128, Mainz, Germany. muellen@mpip-mainz.mpg.de.ORCID http://orcid.org/0000-0001-6630-8786
Akimitsu NaritaMax Planck Institute for Polymer Research, 55128, Mainz, Germany. akimitsu.narita@oist.jp.
Roman FaselEmpa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600, Dübendorf, Switzerland. roman.fasel@empa.ch.ORCID http://orcid.org/0000-0002-1553-6487
Okinawa Institute of Science and Technology Graduate University · JPSwiss Federal Laboratories for Materials Science and Technology · CHInstitute of Structure of Matter · ITJohannes Gutenberg University Mainz · DEMax Planck Institute for Polymer Research · DEUniversity of Bern · CH

Funding

EC | Horizon 2020 Framework Programme (EU Framework Programme for Research and Innovation H2020) 800858EC | Horizon 2020 Framework Programme (EU Framework Programme for Research and Innovation H2020) 881603Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (Swiss National Science Foundation) 200020_182015Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (Swiss National Science Foundation) 200020_212875Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (Swiss National Science Foundation) 205602
6 · The paper itself

Abstract

On-surface synthesis relies on carefully designed molecular precursors that are thermally activated to afford desired, covalently coupled architectures. Here, we study the intramolecular reactions of vinyl groups in a poly-para-phenylene-based model system and provide a comprehensive description of the reaction steps taking place on the Au(111) surface under ultrahigh vacuum conditions. We find that vinyl groups successfully cyclize with the phenylene rings in the ortho positions, forming a dimethyl-dihydroindenofluorene as the repeating unit, which can be further dehydrogenated to a dimethylene-dihydroindenofluorene structure. Interestingly, the obtained polymer can be transformed cleanly into thermodynamically stable polybenzo[k]tetraphene at higher temperature, involving a previously elusive pentagon-to-hexagon transformation via ring opening and rearrangement on a metal surface. Our insights into the reaction cascade unveil fundamental chemical processes involving vinyl groups on surfaces. Because the formation of specific products is highly temperature-dependent, this innovative approach offers a valuable tool for fabricating complex, low-dimensional nanostructures with high precision and yield.

Identifiers

PMID38429274
PMCPMC10907692
OpenAlexW4392359579

What OpenQuestion holds

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LicenceCC BY
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Registered trials

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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.