Quinone photoreduction. II. Mechanism of photoreduction of 9,10-phenanthrenequinone and 2-tert-butyl-9,10-anthraquinone in ethanol

Brennan, J.; Beutel, J.

doi:10.1021/j100844a014

Cited by 12 publications

(1 citation statement)

References 2 publications

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“…The relative rate in hydrogen atom abstractions of excited anthraquinone is very high. The rate is of comparable magnitude as, e.g., chlorine and fluorine atoms (19,30). Therefore, the excited quinones will radicalize almost any polymer exposing C-H groups.…”

Section: Discussionmentioning

confidence: 99%

Photochemical Immobilization of Anthraquinone Conjugated Oligonucleotides and PCR Amplicons on Solid Surfaces

Koch¹,

Jacobsen²,

Fensholdt³

et al. 2000

Bioconjugate Chem.

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Ligand immobilization on solid surfaces is an essential step in fields such as diagnostics, bio sensor manufacturing, and new material sciences in general. In this paper a photochemical approach based on anthraquinone as the chromophore is presented. Photochemical procedures offer special advantages as they are able to generate highly reactive species in an orientation specific manner. As presented here, anthraquinone (AQ) mediated covalent DNA immobilization appears to be superior to currently known procedures. A synthetic procedure providing AQ-phosphoramidites is presented. These reagents facilitate AQ conjugation during routine DNA synthesis, thus enabling the AQ-oligonucleotides to be immobilized in a very convenient and efficient manner. AQ-conjugated PCR primers can be used directly in PCR. When the PCR is performed in solution, the amplicons can be immobilized after the PCR. Moreover, when the primers are immobilized prior to the PCR, a solid-phase PCR can be performed and the amplicons are thus produced directly on the solid support.

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Section: Discussionmentioning

confidence: 99%

Photochemical Immobilization of Anthraquinone Conjugated Oligonucleotides and PCR Amplicons on Solid Surfaces

Koch¹,

Jacobsen²,

Fensholdt³

et al. 2000

Bioconjugate Chem.

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Photochemical cycloaddition of o‐quinones to allenes; 2‐alkylidene‐2,3‐dihydro‐1,4‐dioxins

Bos¹,

Slagt²,

Boleij³

1970

Recl. Trav. Chim. Pays‐Bas

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Phenanthroquinone was added photochemically to allene and nine of its methyl, methoxy and methylthio derivatives. Several 2-alkylidene-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins were isolated; 2 : I-adducts were sometimes found as byproducts. The directiospecificity of the addition was investigated. The stereochemistry and conformation of the adducts are discussed in relation to long-range N M R coupling constants. Tetrachloro-o-benzoquinone was added similarly to methoxyallene. This addition could also be performed thermally.

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Photochemical cycloaddition of 9,10‐phenanthroquinone to allenes III: A kinetic study

Boleij

Bos

1972

Recl. Trav. Chim. Pays‐Bas

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Phenanthroquinone was added photochemically to phenyl-, phenoxy-, t-butyl-, t-butoxy-, cyano-and bromo-allene yielding dihydrodioxin derivatives.Quantum yields and rate constants of the reaction of phenanthroquinone with several substituted allenes were determined. For comparison also quantum yields were measured of the reaction of phenanthroquinone with some corresponding alkenes. The influence of substituents on the reaction rates could satisfactorily be correlated with a PO-YE, relationship of Yumumoru and O m .

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Quinone photoreduction. II. Mechanism of photoreduction of 9,10-phenanthrenequinone and 2-tert-butyl-9,10-anthraquinone in ethanol

Cited by 12 publications

References 2 publications

Photochemical Immobilization of Anthraquinone Conjugated Oligonucleotides and PCR Amplicons on Solid Surfaces

Photochemical Immobilization of Anthraquinone Conjugated Oligonucleotides and PCR Amplicons on Solid Surfaces

Photochemical cycloaddition of o‐quinones to allenes; 2‐alkylidene‐2,3‐dihydro‐1,4‐dioxins

Photochemical cycloaddition of 9,10‐phenanthroquinone to allenes III: A kinetic study

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