| Abstract
| - First examples of persistent oxidation dications from fluoranthene-PAHs namely 1,3,4,6,7,10-hexamethyl- 2 and 3,4-dichloro-1,6,7,10-tetramethylfluoranthene 3, benzo[k]fluoranthene 6, and3,6-dimethyldibenzo[j,l]fluoranthene 9 are reported. Charge delocalization mode and tropicity inthe resulting nonalternant dications are examined. Quenching of the superacid solutions of thedications resulted in the formation of novel 8,8‘-bifluoranthenyls 2a−4a. AM1 was used as an initialguide for dication generation (ΔΔHf° and ionization potentials) and for probing the structures ofthe crowded fluoranthene substrates and their bifluoranthenyls. In selected cases, the dicationsand their neutral precursors were calculated at the B3LYP/6-31G(d,p) level. Charge delocalizationmode (difference in NPA charges) and DFT/GIAO-derived NMR chemical shifts were obtained forcomparison with experiment; aromaticity was assessed via nucleus independent chemical shift(NICS) calculations.
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