Details

Autor(en) / Beteiligte

• Tebi, Stefano
• Paszkiewicz, Mateusz
• Aldahhak, Hazem
• Allegretti, Francesco
• Gonglach, Sabrina
• Haas, Michael
• Waser, Mario
• Deimel, Peter S
• Aguilar, Pablo Casado
• Zhang, Yi-Qi
• Papageorgiou, Anthoula C
• Duncan, David A
• Barth, Johannes V
• Schmidt, Wolf G
• Koch, Reinhold
• Gerstmann, Uwe
• Rauls, Eva
• Klappenberger, Florian
• Schöfberger, Wolfgang
• Müllegger, Stefan

Titel

On-Surface Site-Selective Cyclization of Corrole Radicals

Ist Teil von

• ACS nano, 2017-03, Vol.11 (3), p.3383-3391

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Radical cyclization is among the most powerful and versatile reactions for constructing mono- and polycyclic systems, but has, to date, remained unexplored in the context of on-surface synthesis. We report the controlled on-surface synthesis of stable corrole radicals on Ag(111) via site-specific dehydrogenation of a pyrrole N–H bond in the 5,10,15-tris­(pentafluoro-phenyl)-corrole triggered by annealing at 330 K under ultrahigh-vacuum conditions. We reveal a thermally induced regioselective cyclization reaction mediated by a radical cascade and resolve the reaction mechanism of the pertaining cyclodefluorination reaction at the single-molecule level. Via intramolecularly resolved probing of the radical-related Kondo signature, we achieve real space visualization of the distribution of the unpaired electron density over specific sites within the corrole radical. Annealing to 550 K initiates intermolecular coupling reactions, producing an extended π-conjugated corrole system.