Structural characterization and electrochemical properties of the 3,3′-5,5′-tetra-tert-butyl-4,4′-diphenoquinone

Crystals of the 3,3′-5,5′-tetra-tert-butyl-4,4′-diphenoquinone (TTBDQ) in the reaction mixture DCM/MeOH (1:1, v/v) were obtained as a result of CC coupling reaction of the sterically hindered phenol (2,6-di-tert-butylphenol, DTBP) using the binuclear Co(II) complexes. The oxidation product (TTBDQ), C28H40O2, crystallizes in the space group P1¯ with one-half molecule in the asymmetric unit and the other half generated by an inversion centre. The diphenoquinone moiety is planar within ±0.016(3) Å. The crystal structure is stabilized by intramolecular CH⋯O hydrogen bonds. The spectroscopic and electrochemical properties of the TTBDQ also have been studied.