Beilstein J. Org. Chem.2025,21, 515–525, doi:10.3762/bjoc.21.39
; perfluorobenzylation; photochemistry; Introduction
The revolution of small organic molecules in the semiconductor industry continues to progress, replacing some silicon and metal-based electronic components. Acenes, such as anthracene (ANTH) and its higher homologues, represent some of the most studied materials that
dimeric molecules, instead of expected 9,10-(perfluoroalkyl)2ANTH [26].
To the best of our knowledge, perfluorobenzylation of anthracene has not been reported prior to this study. The only PAH perfluorobenzylations were reported by our group: with CORA using gas-phase solvent-free reactions in sealed
used for the perfluorobenzylation of PERY were used [22]. 9,10-ANTH(Br)2 and BnFI were dissolved and heated to 160 °C in PhCN in the presence of either Cu powder (22 h) or Na2S2O3 (4 h). According to the 1H NMR spectra of the filtered product mixtures, the reaction with Cu showed poor conversion, but
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Graphical Abstract
Scheme 1:
List of reactions, experimental conditions and yields studied in this work.