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Tales of the Unexpected: Selectivity of Nucleophilic Additions to Zigzag Nanographene Diones
preprintsubmitted on 08.12.2020, 15:00 and posted on 09.12.2020, 12:50 by Peter Ribar, Leos Valenta, Tomas Solomek, Michal Juricek
Nucleophilic addition of carbon-centered nucleophiles to nanographene ketones represents a valuable late-stage method for the functionalization of zigzag nanographenes, but its use is rare in the chemical literature. Using two model systems, non-Kekulé triangulene-4,8-dione and Kekulé anthanthrone, we identify unexpected regioselectivities and uncover the rules that govern these reactions. Considering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar, this method enables synthesis and exploration of hitherto unknown functionalized nanographenes.