779976-14-6

Upstream product

• 31366-25-3 tetrathiafulvalene 
• 527-17-3 Duroquinone 
• 582-16-1 2,7-dimethylnaphthalene 
• 121-44-8 triethylamine 

Downstream Products

• 527-17-3 Duroquinone 
• 70128-24-4 C₁₀H₁₂O₂^(2-) 
• 75877-78-0 (4-chlorophenyl)diazenyl radical 

Relevant academic research and scientific papers

EOSIN Y SENSITIZED REDUCTION OF QUINONES TO THEIR PERSISTENT RADICAL ANIONS

Eosin Y sensitized efficiently the reduction of duroquinone and anthraquinone-2-sulfonate to their persistent radical anions in aqueous 2-propanol in the presence of triethanolamine.

Zinc Porphyrin Sensitized Reduction of Simple and Functional Quinones in Micellar Systems

The photoinduced reduction of duroquinone (DQ) and a long-chain substitued duroquinone (C11DQ) by zinc porphyrin was studied by means of laser photolysis techniques in micellar solution.The mean time required for intramicellar electron transfer is 0.2 μs

Structure and function of quinones in biological solar energy transduction: A high-frequency d-band EPR spectroscopy study of model benzoquinones

Quinones are utilized as charge-transfer cofactors in a wide variety of reactions that are crucial for photosynthesis and respiration. In photosynthetic protein complexes, both Type I and Type II, including oxygenic and anoxygenic reaction centers contain quinone cofactors that are known to participate in electron- and proton-transfer processes. Type II reaction centers, purple bacterial reaction centers, and photosystem II utilize benzoquinone molecules, ubiquinone, and plastoquinone, respectively, to facilitate proton-coupled electron transfer reactions. Here, we report a systematic study of the principal components of the g-tensor of an extensive library of model benzosemiquinone anion radicals in both protic (2-isopropanol) and aprotic (dimethyl sulfoxide) solvents using high-frequency EPR spectroscopy. A detailed comparison of the experimental g-values of the benzosemiquinone models at D-band EPR frequency allows for the discrimination of substituent effects and solvent hydrogen bonds on the principal components of the g-tensor. Further, we compare the primary plastosemiquinone, QA-, of photosystem II with the substituent and solvent hydrogen bond effects of benzosemiquinone models in vitro. This study significantly extends the experimental basis for elucidating the role of both molecular structure and interactions with environment on the functional tuning of quinone cofactors in biological solar energy transduction.

NADPH and ferredoxin:NADP+ oxidoreductase-dependent reduction of quinones and their reoxidation

Molecular oxygen uptake was initiated by adding NADPH (1 mM) to the buffered medium containing 0.6 μM spinach ferredoxin:NADP+ oxidoreductase and 20 μM quinone (plastoquinone-2, decyl-plastoquinone, decyl-ubiquinone, or duroquinone). At pH 7.7 the rate of oxygen uptake was 2- to 12-fold higher during an initial phase (V1) than in a subsequent phase (V2). Except for duroquinone, the initial rate of oxygen consumption was ca. 2.7-fold higher in alkaline than in acidic medium. Ferredoxin was not essential, although it stimulated the reaction investigated. Oxygen uptake was not detectable with plastoquinone-9 or α-tocoquinone. The possible mechanisms of the NADPH and ferredoxin:NADP oxidoreductase dependent reduction of some quinones and their reoxidation are discussed.

Wide-Band, Time-Resolved Photoacoustic Study of Electron-Transfer Reactions: Photoexcited Magnesium Porphyrin and Quinones

Wide-band, time-resolved, pulsed photoacoustics has been employed to study the electron-transfer reaction between a triplet magnesium porphyrin and various quinones in polar and nonpolar solvents.The reaction rate constants are near encounter limited.The yield of triplet state is 70percent in both solvents.The yield of ions is 85percent in the former and zero in the latter, in agreement with spin dephasing time and escape times from the Coulomb wells in the two solvents.In methanol the plot of measured heat output versus quinone redox potential is linear.This implies that the entropy of electron transfer is constant through the series, but it may not be negligible.

Nitrogen Dioxide and Related Free Radicals: Electron-transfer Reactions with Organic Compounds in Solutions containing Nitrite or Nitrate

The absolute rate constants for the reaction of NO32-. (formed by one-electron reduction of nitrate) with oxygen, benzoquinone, and methyl viologen have been determined by pulse radiolysis.Experiments have shown that such reactions can occur in competition with the hydrolysis reaction leading to NO2. and that the formation of the latter can be catalysed by the presence of hydrogen or ammonium ions.Absolute rate constants for the oxidation of the phenothiazine derivative metiazinic acid, of 2,2'-azinobis-(3-ethyl-2,3-dihydrobenzothiazole-6-sulphonate), of ascorbate, and of dihydroxyfumarate by NO2. have also been measured.

CIDEP Study of Durosemiquinone Radical in Various Solvents

F-pair polarization and triplet mechanism (TM) polarization of durosemiquinone radical produced by light irradiation of duroquinone-phenol systems were discriminated at 260 K in a simple way based on the analysis of the enhancement factors in the steady-state method with intermittent light irradiation.Both polarizations are not so sensitive to viscosity or polarity of solvents.TM enhancement factor is nearly constant (-0.8) in wide range of viscosity (2.5-25 cP, 1 cP=0.001 Pa s).F-pair polarization is suppressed in some extent by halogenated solvents while TM polarization is not affected by such solvents.

Dimer Cation Formation in Anionic Microemulsion Media. Duroquinone-Sensitized Photooxidation of 2,6-Dimethylnaphthalene and Tetrathiafulvalene

Flash photolysis studies using a ruby laser (λ=347 nm, doubled line) were performed on the systems duroquinone (DQ)/2,6-dimethylnaphthalane (DMN) and DQ/tetrathiafulvalene (TTF) principally in sodium hexadecyl sulfate (SCS) microemulsion media.Electron transfer from both DMN and TTF to triplet duroquinone with efficient charge separation to produce the product cations and anion was observed in these media.Identical experiments performed in homogeneous media demonstrated electron transfer but with less efficient charge separation and consequently lower product ion yields.Dimer cation formation of both DMN and TTF, i.e., (DMN)2+ and (TTF)2+, in the anionic microemulsion media was readily detected.The formation of (TTF)2+ was reverified by pulse radiolysis experiments.Although tetrathiafulvalene stacks easily in organic conducting salts and thus should have no difficulty in obtaining the supposed sandwichlike configuration of the dimer, no previous reports announce its detection.Dimer cation formation of aromatic compounds in microemulsion media is unique in itself since the majority of previous studies of this type involved γ irradiation of substrate solubilized in glassy alkane matrices at low temperatures (77 K).The dimer formation constant for DMN was evaluated graphically as K=4.76*102.