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    ?,??-diamino- p-tetrafluoroquinodimethane: stability of one- and two-electron oxidized species and fixation of molecular oxygen
    (American Chemical Society, 2021) Mahata, Alok; Chrysochos, Nikolas; Krummenacher, Ivo; Chandra, S.; Braunschweig, H.; Schulzke, C.; Sarkar, B.; Yıldız, Cem Burak; Jana, A.
    Herein, we report the synthesis, characterization, and reactivity of ?,??-diamino-p-tetrafluoroquinodimethane, a p-tetrafluorophenylene-bridged monosubstituted carbene-based Thiele's hydrocarbon A. The compound exhibits a reversible two-step one-electron oxidation with a marginally stable radical cation state B. The in situ formation of the radical cation could be confirmed by electron paramagnetic resonance spectroscopy.
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    ?,??-Diamino-p-quinodimethanes with three stable oxidation states
    (American Chemical Society, 2020) Mahata, Alok; Chandra, Shubhadeep; Maiti, Avijit; Rao, D. Krishna; Yıldız, Cem Burak; Sarkar, Biprajit; Jana, Anukul
    Herein, we report the rational design, synthesis, and characterization of ?,??-diamino-substituted-p-quinodimethanes, which are a group of partially substituted p-quinodimethanes. These exhibit two reversible one-electron redox steps and electrochromism in the ultraviolet, visible, and near-infrared regions. We were able to isolate the crystalline compounds of all three oxidation states: neutral, radical cation, and dication. The obtained results not only create the bridge between p-quinodimethane and ?,?,??,??-tetrasubstituted-p-quinodimethane, but also demonstrate the straightforward modular approach for the synthesis of ?-conjugated open-shell compounds.