Fig. 5: Redox behavior of methyl-substituted derivative 1c and its derivative 1c-2H. | Nature Communications

Fig. 5: Redox behavior of methyl-substituted derivative 1c and its derivative 1c-2H.

From: Diverse redox-mediated transformations to realize the para-quinoid, σ-bond, and ortho-diphenoquinoid forms

Fig. 5

a Preparation of hydride adduct 1c-2H via dication salt 1c2+[SbCl6–]2. (i) Magic blue (2.0 eq) in CH2Cl2, (ii) NaBH4 in MeCN. Redox interconversion between 1c-2H and 1c-2H2+[SbCl6–]2 via intermediary radical cation. b UV−vis spectra of 1c (black), 1b-2H (yellow), and 1c-2H (violet) in CH2Cl2. c X-ray crystal structures (ORTEP drawings) of 1c-2H determined at 150 K. Solvent molecules are omitted for clarity. Thermal ellipsoids are shown at 50% probability. The bond lengths are shown in the accompanying table. The calculated values are shown in italics. Color code: atoms, C: gray, O: red, S: yellow, H: light blue. d Electrochemical measurements conducted on 1c-2H at 298 K in CH2Cl2 containing 0.1 M [Bu4N+][BF4–] as the supporting electrolyte. Change in the UV−vis−NIR spectrum from (e) 1c-2H (19.2 μM) to 1c-2H•+ (1st stage) and (f) from the as-prepared 1c-2H•+ to 1c-2H2+ (2nd stage) upon adding several aliquots of magic blue in CH2Cl2.

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