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

Alexander Riss (), Marcus Richter, Alejandro Pérez Paz, Xiao-Ye Wang, Rajesh Raju, Yuanqin He, Jacob Ducke, Eduardo Corral, Michael Wuttke, Knud Seufert, Manuela Garnica, Angel Rubio, Johannes V. Barth, Akimitsu Narita, Klaus Müllen, Reinhard Berger, Xinliang Feng, Carlos-Andres Palma () and Willi Auwärter
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Alexander Riss: Technical University of Munich
Marcus Richter: Dresden University of Technology
Alejandro Pérez Paz: Yachay Tech University
Xiao-Ye Wang: Max Planck Institute for Polymer Research
Rajesh Raju: Max Planck Institute for Polymer Research
Yuanqin He: Technical University of Munich
Jacob Ducke: Technical University of Munich
Eduardo Corral: Technical University of Munich
Michael Wuttke: Max Planck Institute for Polymer Research
Knud Seufert: Technical University of Munich
Manuela Garnica: Technical University of Munich
Angel Rubio: Universidad del País Vasco
Johannes V. Barth: Technical University of Munich
Akimitsu Narita: Max Planck Institute for Polymer Research
Klaus Müllen: Max Planck Institute for Polymer Research
Reinhard Berger: Dresden University of Technology
Xinliang Feng: Dresden University of Technology
Carlos-Andres Palma: Technical University of Munich
Willi Auwärter: Technical University of Munich

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-15210-2

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