Molecular complexes of 3,3?,5,5?-tetrahalo-4,4?-diphenoquinones. 1. synthesis and properties of 3,3?,5,5?-tetrahalo-4,4?-diphenoquinones

Popov, Yu. P.; Литвинов, В. П.; Sokol'skaya, I. L.

doi:10.1007/bf00951221

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“…Analogous attempts to make tetrahalodiphenoquinones 21 and 22 by direct oxidative coupling of dihalophenols were unsuccessful; instead, the diphenoquinones were synthesized in 97% and 98% yields, respectively, by using PIDA to oxidize the corresponding 3,3′,5,5′-tetrahalo-4,4′-dihydroxybiphenyls 23 and 24 . These precursors were made in 72% and 89% yields, respectively, by modifying published procedures for using Cl 2 or Br 2 to halogenate 4,4′-dihydroxybiphenyl. − …”

Section: Resultsmentioning

confidence: 99%

“…109 Electron-donating substituents appear to lower the potential of diphenoquinones and electron-withdrawing substituents to increase it, as suggested by earlier studies of tetramethyldiphenoquinone 16, tetra-tertbutyldiphenoquinone 17, 3,3′,5,5′-tetrahalodiphenoquinones (F, Cl, Br, and I), and other compounds. 72,99,103 This earlier work established that diphenoquinones have electrochemical properties of significant interest. However, few electrochemical analyses of large sets of diphenoquinones have been carried under uniform conditions to provide a foundation for understanding how the structures and redox properties of these compounds are correlated.…”

Section: ■ Introductionmentioning

confidence: 99%

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Diphenoquinones Redux

et al. 2022

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Benzoquinones can undergo reversible reductions and are attractive candidates for use as active materials in green carbon-based batteries. Related compounds of potential utility include 4,4′-diphenoquinones, which have extended quinonoid structures with two carbonyl groups in different rings. Diphenoquinones are a poorly explored class of compounds, but a wide variety can be synthesized, isolated, crystallized, and fully characterized. Experimental and computational approaches have established that typical 4,4′-diphenoquinones have nearly planar cores in which two cyclohexadienone rings are joined by an unusually long interannular CC bond. Derivatives unsubstituted at the 3,3′,5,5′-positions react readily by hydration, dimerization, and other processes. Association of diphenoquinones in the solid state normally produces chains or sheets held together by multiple C–H···O interactions, giving structures that differ markedly from those of the corresponding 4,4′-dihydroxybiphenyls. Electrochemical studies in solution and in the solid state show that diphenoquinones are reduced rapidly and reversibly at potentials higher than those of analogous benzoquinones. Together, these results help bring diphenoquinones into the mainstream of modern chemistry and provide a foundation for developing redox-active derivatives for use in carbon-based electrochemical devices.

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Section: Resultsmentioning

confidence: 99%