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

• DOI: 10.1038/s41467-020-15210-2
• Publication Date: 2020-03-20T11:03:13Z
• Authors: 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; Willi Auwärter
• Keywords: algorithm; Science; Q; graphene; azomethine ylides; Article; ddc:; CU(111); total-energy calculations; boron-nitride; azide-alkyne cycloaddition; on-surface synthesis; dehalogenation; 1,3-dipolar cycloadditions

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