AI Article Synopsis
- - Radical cyclization is an effective method for creating mono- and polycyclic structures, but its application in on-surface synthesis has not been thoroughly investigated until now.
- - This research demonstrates the controlled synthesis of stable corrole radicals on a silver surface through targeted dehydrogenation and subsequent cyclization at specific temperatures.
- - The study successfully visualizes the unpaired electron density in the radical and explores intermolecular reactions that occur at higher temperatures, leading to more complex corrole structures.
Article Abstract
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.
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| http://dx.doi.org/10.1021/acsnano.7b00766 | DOI Listing |
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