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Updated: Jul 12, 2025

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Luminescent Chiral Furanol-PAHs via Straightforward Ni-Catalysed Csp2 -F Functionalization: Mechanistic Insights into
Judith Sala1, Lorena Capdevila1, Cristina Berga1
1Institut de Química Computacional i Catàlisi (IQCC) and, Departament de Química, Universitat de Girona, Campus Montilivi, 17003, Girona, Catalonia, Spain.
Abstract:
Here we report the stepwise synthesis of new nanographenes (NGs) and polycyclic aromatic hydrocarbons (PAHs) obtained via Scholl ring fusion applied at aromatic homologation compounds, which are obtained through one-step Ni-catalysed Csp2 -F functionalization. The latter are rapidly accessed valid precursors for the Scholl reaction, and screening of experimental conditions allowed us to describe for the first time furanol-bearing PAHs. Mechanistic insights are obtained by DFT to rationalize the formation of the furanol PAHs under moderately acidic conditions. All PAHs and NGs synthesized show moderate/weak fluorescent properties, and all PAHs crystallized show some degree of curvature and are obtained as racemic mixtures. Enantiomeric separation by chiral HPLC of one furanol-bearing PAH allowed the study of their chiroptical CD properties.
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