Benzo[ <i>d</i> ]imidazole Based Organic Photocatalyst for Trifluoromethylation of Polyaromatic Hydrocarbons

The surge of organofluorine compounds, particularly incorporation of a –CF 3 group in organic molecules for pharmaceutical and materials sectors demands development of a mild and regioselective trifluoromethylation route. In this work, procarbenic benzo[ d ]imidazole based organic photocatalysts C1 and C2 enabled mild, regioselective trifluoromethylation, addressing the demand of –CF 3 incorporation in polyaromatic hydrocarbons (PAHs). These photocatalysts showed intense ligand-to-ligand charge transfer absorption in the UV (λ abs ∼ 280 nm) and low-negative quasi-reversible reductions ( E red = −0.91 and −1.11 V vs SCE for C1 and C2 ). Both emitted deep-blue 1 LC fluorescence at RT (375–390 nm) and acted as strong photo-oxidants ( E C(II)*/C(I) ∼ 2.70 V vs SCE), enabling efficient metal- and additive-free mono(trifluoromethylation) of polyaromatic hydrocarbons.