Peroxide Induced Reduction of 9,10-Anthraquinone by Sodium Borohydride in Diglyme<sup>1</sup>

Panson, Gilbert S.; Weill, C. Edwin

doi:10.1021/jo01353a003

Cited by 9 publications

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“…13 C NMR spectra for all of the synthesized compounds are given in the Supporting Information. 9,10-Anthraquinone was reduced to the corresponding diol by H 2 O 2 -induced reduction with sodium borohydride, as described in the literature …”

Section: Methodsmentioning

confidence: 99%

Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

et al. 2005

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Amide-linked spiropyran-anthraquinone (SP-AQ) conjugates were shown to mediate ZnTPPS(4-)-photosensitized transmembrane reduction of occluded Co(bpy)3(3+) within unilamellar phosphatidylcholine vesicles by external EDTA. Overall quantum yields for these reactions were dependent upon the isomeric state of the dye; specifically, 30-35% photoconversion of the closed-ring spiropyran (SP) moiety to the open-ring merocyanine (MC) form caused the quantum yield to decrease by 6-fold in the simple conjugate and 3-fold for an analogue containing a lipophilic 4-dodecylphenoxy substituent on the anthraquinone moiety. Transient spectroscopic and fluorescence quenching measurements revealed that two factors contributed to these photoisomerization-induced changes in quantum yields: increased efficiencies of fluorescence quenching of 1ZnTPPS4- by the merocyanine group and lowered transmembrane diffusion rates of the merocyanine-containing redox carriers. Transient spectrophotometry also revealed the sequential formation and decay of two reaction intermediates, identified as 3ZnTPPS4- and a species with the optical properties of a semiquinone radical. Kinetic profiles for Co(bpy)3(3+) reduction under continuous photolysis in the presence and absence of added ionophores indicated that transmembrane redox mediated by SP-AQ was electroneutral, but reaction by the other quinone-containing mediators was electrogenic. The minimal reaction mechanism suggested from the combined studies is oxidative quenching of vesicle-bound 3ZnTPPS4- by the anthraquinone unit, followed by either H+/e- cotransport by transmembrane diffusion of SP-AQH* or, for the other redox mediators, semiquinone anion-quinone electron exchange leading to net transmembrane electron transfer, with subsequent one-electron reduction of the internal Co(bpy)3(3+). Thermal one-electron reduction of Co(bpy)3(3+) by EDTA is energetically unfavorable; the photosensitized reaction therefore occurs with partial conversion of photonic energy to chemical and transmembrane electrochemical potentials.

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Section: Methodsmentioning

confidence: 99%

Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

et al. 2005

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Anthraquinone

Cofrancesco¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Obtaining anthraquinone by oxidizing anthracene with bichromate and sulfuric acid later became the first commercial method for the manufacture of anthraquinone from anthracene. For many years, anthraquinone provided the dyestuff industry with one of the greatest and most prolific building blocks for the manufacture of valuable dyestuffs noted for their outstanding fastness properties. However, in recent times production has fallen off considerably due to the high cost of manufacturing and the discovery of other classes of dyestuffs with good fastness properties. When sublimed, anthraquinone forms a pale yellow, crystalline material, needlelike in shape. It melts at 286°C and boils at 379–381°C. At much higher temperatures, decomposition occurs. Anthraquinone has only a slight solubility in alcohol or benzene and is best recrystallized from glacial acetic acid or high boiling solvents such as nitrobenzene or dichlorobenzene. It is very soluble in concentrated sulfuric acid. In general, anthraquinone is a relatively inert compound exhibiting stability toward oxidation. Only the reduction products involving the keto groups are of any academic or industrial importance. In the dyestuff industry, anthraquinone still ranks high as an intermediate for the production of dyes and pigments having properties unattainable by any other class of dyes or pigments. At this writing (1993) the only two processes for its production are by the Friedel‐Crafts reaction utilizing benzene, phthalic anhydride, and anhydrous aluminum chloride, and by the vapor‐phase catalytic oxidation of anthracene, the latter being preferred. Anthraquinone is a comparatively safe compound. It is a mild allergen and may cause skin irritation. It presents only a slight fire hazard on exposure to heat. The use of benzene in the Friedel‐Crafts process presents serious safety and health problems. Besides its major use in the manufacture of intermediates for anthraquinone dyes and pigments, anthraquinone is finding increasing interest as a catalyst in wood pulping in polymerization of various materials for plastics, and in the isomerization of vegetable oils.

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Neuere Methoden der präparativen organischen Chemie IV Anwendung von komplexen Borhydriden und von Diboran in der organischen Chemie

Schenker¹

1961

Angewandte Chemie

102

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Peroxide Induced Reduction of 9,10-Anthraquinone by Sodium Borohydride in Diglyme¹

Cited by 9 publications

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Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

Anthraquinone

Neuere Methoden der präparativen organischen Chemie IV Anwendung von komplexen Borhydriden und von Diboran in der organischen Chemie

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Peroxide Induced Reduction of 9,10-Anthraquinone by Sodium Borohydride in Diglyme1

Cited by 9 publications

References 0 publications

Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules

Anthraquinone

Neuere Methoden der präparativen organischen Chemie IV Anwendung von komplexen Borhydriden und von Diboran in der organischen Chemie

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Peroxide Induced Reduction of 9,10-Anthraquinone by Sodium Borohydride in Diglyme¹