The Photolysis Of The Endoperoxide Of 9,10-Diphenylanthracene

Drews, W.; Shimidt, R.; Brauer, H.‐D.

doi:10.1016/0009-2614(80)80065-0

Cited by 51 publications

(20 citation statements)

References 14 publications

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“…The absorption and fluorescence of the product are benzene-like due to the loss of aromaticity in the central ring and are therefore shifted to the UV (from 400 to 280 nm). This endoperoxide is thermally stable at room temperature [5,6], it is photochemically unstable giving back ADPA [7,8] but at the wavelengths used the endoperoxide does not absorb (l > 300 nm). This dye was chosen for the measurement of 1 O 2 because of its high solubility in water, its high rate constant for reaction with 1 O 2 [9,10], the thermal stability of the endoperoxide formed and the fact that it does not absorb light at the wavelength used for irradiation of the 1 O 2 source (465 or 488 nm).…”

Section: Introductionmentioning

confidence: 99%

Production of singlet oxygen by Ru(dpp(SO3)2)3 incorporated in polyacrylamide PEBBLES

Moreno

Monson

Reddy

et al. 2003

Sensors and Actuators B: Chemical

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Polyacrylamide (PAA) and amine-functionalized PAA (AFPAA) nanoparticles with disulfonated 4,7-diphenyl-1,10-phenantroline ruthenium (Ru(dpp(SO 3 ) 2 ) 3 ) have been prepared. The nanoparticles produced have a hydrodynamic radius of 20-25 nm.The amount of singlet oxygen ( 1 O 2 ) produced by Ru(dpp(SO 3 ) 2 ) 3 as been measured using anthracene-9,10-dipropionic acid (ADPA). A kinetic model for the disappearance of ADPA, by steady state irradiation of Ru(dpp(SO 3 ) 2 ) 3 at 465 nm, has been developed taking also into account a consumption not mediated by 1 O 2 . This direct consumption of ADPA is evaluated by irradiating in the presence of NaN 3 and is about 30% of the total. All the experimental results are very well described by the model developed, both for free Ru(dpp(SO 3 ) 2 ) 3 and with this dye incorporated in the nanoparticles.It is found that the polyacrylamide matrix does not quench the 1 O 2 produced, allowing it to reach the external solution of the nanoparticles and react with ADPA. When the matrix possesses amine groups, AFPAA, the amount of 1 O 2 that reacts with ADPA is slightly reduced, 60%, but most of the 1 O 2 produced can still leave the particles and react with external molecules. The particles produced may therefore be used as sources of 1 O 2 in photodynamic therapy (PTD) of cancers. The fact that those nanoparticles do not quench significantly the 1 O 2 makes possible the future development of 1 O 2 sensors based on PAA nanoparticles with the appropriate sensor molecule enclosed. #

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Section: Introductionmentioning

confidence: 99%

Production of singlet oxygen by Ru(dpp(SO3)2)3 incorporated in polyacrylamide PEBBLES

Moreno

Monson

Reddy

et al. 2003

Sensors and Actuators B: Chemical

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“…In this way the resulting fluorescence volume of the UV-affected anthracene crystallites was scanned through the different temperature settings. These experimental conditions were close to those used for investigating the chargetransfer complexes in thin films of anthracene (25)(26)(27). Indeed, the very short period of UV irradiation used in this experiment (2 min of 0.3 W/cm 2 ) should only affect a thin layer of the irradiated material.…”

Section: Mass-balance Analysis Of Anthracene Particulate Materialsmentioning

confidence: 54%

“…It would be plausible for both the experimental conditions used. This involves the formation of long-living charge-transfer complexes, which are known (25)(26)(27) to quench anthracene fluorescence. In this respect, Kondratenko and Lopatkin (27) have discussed the formation of charge-transfer complexes for anthracene and its photooxide products, both the short-lived (anthracene peroxide) as well as the long-lived (anthraquinone) ones.…”

Section: Mass-balance Analysis Of Anthracene Particulate Materialsmentioning

confidence: 99%

Photochemical Study of Anthracene Crystallites by Fourier Transform Spectroscopic Imaging¶

Sluszny

Bulatov

Gridin

et al. 2007

Photochemistry and Photobiology

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Fourier transform–based spectroscopic imaging was used for direct, time‐resolved, analysis of UV‐irradiated anthracene crystallites. Well‐resolved fluorescence spectra were obtained at a spatial resolution of 1 μm. The appearance of such photochemical by‐products as dianthracene and anthraquinone was monitored throughout the irradiation experiments. Under deaerated conditions, photolysis of anthracene was accompanied by formation of dianthracene. When performed under aerated conditions, however, the spectral data indicated formation of both dianthracene and anthraquinone. Spectral features obtained for the directly monitored photolysis of anthracene are discussed in respect to the structural and compositional modifications in such crystallites. Capabilities of the spectral imaging device for the quantification of the photochemical products of anthracene are discussed.

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“…Anthracene-endoperoxide derivatives have also been reported to cause photodegradation [27,28], wherein C-O bond cleavage predominates in anthracene derivatives with substituents that facilitate unpaired electron delocalization, such as diphenylanthracene-endoperoxide (DPA-EPO). In this context, Drews et al demonstrated that DPA-EPO reacts differently at two different wavelengths of light [27], resulting in cleavage of the C-O bond at one wavelength and that of the O-O bond at another.…”

Section: Plos Onementioning

confidence: 99%

Mechanism for the photodegradation of 9,10-dibutoxyanthracene in the presence of air

Seto

Sato

Iuchi³

et al. 2022

PLoS ONE

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The photoreactivity of anthracene has been previously verified for a range of its derivatives. 9,10-Dibutoxyanthracene is commonly used as an electron transfer sensitizer for photopolymerization because of its favorable optical properties. This study experimentally demonstrated that 9,10-dibutoxyanthracene produces an endoperoxide species upon reaction with the oxygen present in air. A secondary decomposition product formed during the photodecomposition of the endoperoxide species was also isolated and identified. The proposed reaction pathway is supported by singlet oxygen scavenger studies and calculations of the singlet–triplet transition energies. Our findings suggest that 9,10-dibutoxyanthracene can be used as a photo-induced oxygen scavenger.

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The Photolysis Of The Endoperoxide Of 9,10-Diphenylanthracene

Cited by 51 publications

References 14 publications

Production of singlet oxygen by Ru(dpp(SO3)2)3 incorporated in polyacrylamide PEBBLES

Production of singlet oxygen by Ru(dpp(SO3)2)3 incorporated in polyacrylamide PEBBLES

Photochemical Study of Anthracene Crystallites by Fourier Transform Spectroscopic Imaging¶

Mechanism for the photodegradation of 9,10-dibutoxyanthracene in the presence of air

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