Pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs): Syntheses of difluorinated subfamily and their properties

•Difluorinated PAHs were synthesized by the cyclization of fluoroalkenes or -allenes with a Pd(II)- or an In(III) catalyst.•The 19F NMR signals of the bay fluorines were shifted downfield by 8–14ppm (vic-difluoro) and 11–19ppm (non-vic-difluoro).•The fluorine introduction into PAHs increased their solubilities, exemplified by that of 6,7-difluoropicene (5.4wt%) in THF.•The HOMO–LUMO energy gaps of fluorinated PAHs were smaller than that of the corresponding fluorine-free PAH by 0.02–0.26eV.•The HOMO energy levels of fluorinated PAHs were lowered by 0.10–0.22eV, suggesting their resistance to aerial oxidation.