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Tales of the Unexpected: Selectivity of Nucleophilic Additions to Zigzag Nanographene Diones

preprint
submitted 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.

Funding

ERC Starting Grant (M.J./716139, INSPIRAL)

Swiss National Science Foundation (T.Š./PZ00P2_174175)

Swiss National Science Foundation (M.J./PZ00P2_148043)

Swiss National Science Foundation (M.J./PP00P2_170534)

Experientia Foundation (T.Š.)

History

Email Address of Submitting Author

michal.juricek@chem.uzh.ch

Institution

University of Zurich

Country

Switzerland

ORCID For Submitting Author

0000-0001-5595-431X

Declaration of Conflict of Interest

No conflict of interest.

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