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  Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions

Riss, A., Richter, M., Pérez Paz, A., Wang, X.-Y., Raju, R., He, Y., et al. (2020). Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions. Nature Communications, 11(1): 1490. doi:10.1038/s41467-020-15210-2.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-EDF3-E Version Permalink: http://hdl.handle.net/21.11116/0000-0006-0FFA-1
Genre: Journal Article

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41467_2020_15210_MOESM1_ESM.pdf (Supplementary material), 11MB
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https://dx.doi.org/10.1038/s41467-020-15210-2 (Publisher version)
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 Creators:
Riss, A.1, Author
Richter, M.2, Author
Pérez Paz, A.3, 4, 5, Author
Wang, X.-Y.6, 7, Author
Raju, R.6, Author
He, Y.1, Author
Ducke, J.1, Author
Corral, E.1, Author
Wuttke, M.6, Author
Seufert, K.1, Author
Garnica, M.1, 8, Author
Rubio, A.5, 9, 10, Author              
Barth, J. V.1, Author
Narita, A.6, 11, Author
Müllen, K.6, 12, Author
Berger, R.2, Author
Feng, X.2, Author
Palma, C.-A.1, 13, Author
Auwärter, W.1, Author
Affiliations:
1Physics Department E20, Technical University of Munich, ou_persistent22              
2Department for Molecular Functional Materials, Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Dresden University of Technology, ou_persistent22              
3School of Physical Sciences and Nanotechnology, Yachay Tech University, ou_persistent22              
4Chemistry Department, College of Science, United Arab Emirates University (UAEU), ou_persistent22              
5Nano-Bio Spectroscopy Group and ETSF, Universidad del País Vasco, ou_persistent22              
6Max Planck Institute for Polymer Research, ou_persistent22              
7State Key Laboratory o fElemento-Organic Chemistry, College of Chemistry, Nankai University, ou_persistent22              
8Instituto Madrileño de Estudios Avanzados en Nanociencia (IMDEA-Nanociencia), ou_persistent22              
9Theory Group, Theory Department, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society, ou_2266715              
10Center for Free−Electron Laser Science and Department of Physics, University of Hamburg, ou_persistent22              
11Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, ou_persistent22              
12Institute of Physical Chemistry, Johannes Gutenberg-University Mainz, ou_persistent22              
13Institute of Physics, Chinese Academy of Sciences, ou_persistent22              

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 Abstract: The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of π-conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains to be demonstrated with high yield and selectivity. Here we present the synthesis of polyaromatic chains on metallic substrates, insulating layers, and in the solid state. Scanning probe microscopy shows the formation of azaullazine repeating units on Au(111), Ag(111), and h-BN/Cu(111), stemming from intermolecular homo-coupling via cycloaddition reactions of CN-substituted polycyclic aromatic azomethine ylide (PAMY) intermediates followed by subsequent dehydrogenation. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry demonstrates that the reaction also takes place in the solid state in the absence of any catalyst. Such intermolecular cycloaddition reactions are promising methods for direct synthesis of regioregular polyaromatic polymers on arbitrary insulating surfaces.

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Language(s): eng - English
 Dates: 2019-06-232020-02-242020-03-20
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1038/s41467-020-15210-2
 Degree: -

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Grant ID : 664878
Funding program : Horizon 2020 (H2020)
Funding organization : European Commission (EC)

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Title: Nature Communications
  Abbreviation : Nat. Commun.
Source Genre: Journal
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Affiliations:
Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 11 (1) Sequence Number: 1490 Start / End Page: - Identifier: ISSN: 2041-1723
CoNE: https://pure.mpg.de/cone/journals/resource/2041-1723