Chemiluminescence in the oxidation of europium β-diketonates by dimethyldioxirane

Nucleophilic anions such as Cl(-), I(-), Br(-), t-BuO(-), O(2)(-) and OH(-) efficiently catalyze the decomposition of dimethyldioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFD). Singlet oxygen ((1)O(2)) is formed in these catalytic reactions, as demonstrated by the characteristic infrared chemiluminescence (IR-CL) at 1268 nm. The yield of (1)O(2) generation, measured by the IR-CL method, lies in the range between 2 and 98%, which depends on the particular anion employed. For the bromide ion, the catalytic decomposition of the dioxirane is in competition with the oxidation of Br(-) to elemental bromine.

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“…Such unusual chemiluminescence offers new perspectives for further development and exploration. 3,11,[38][39][40]…”

Section: Discussionmentioning

confidence: 99%

Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

Adam

Казаков

Казаков³

et al. 2004

Photochem Photobiol Sci

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“…dimethyldioxirane. 16 Additional support for the proposed nontrivial mode of lanthanide chemiexcitation comes from photoluminescence measurements made after diminution of CL in the system Eu(fod) 3 /DMNE, which disclosed one order of magnitude decrease in intensity of europium photoluminescence. This indicates drastic changes in the europium coordination sphere, presumably associated with oxidation of the ligands by 1 O 2 .…”

Section: S-2 Esi †)mentioning

confidence: 94%

A novel chemiluminescence from the reaction of singlet oxygen with β-diketonates of europium(iii), neodymium(iii) and ytterbium(iii)

Казаков

Safarov

2014

Photochem Photobiol Sci

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Decomposition of 1,4-dimethylnaphthalene endoperoxide, which is the source of singlet oxygen, in the presence of β-diketonates of europium(III), neodymium(III) and ytterbium(III) is accompanied by bright chemiluminescence (CL) in visible and near infra-red spectral region due to characteristic emission from the lanthanides at λmax = 615 and 710 nm ((5)D0→(7)F2 and (5)D0→(7)F4 transitions of Eu(3+)), 900 nm ((4)F3/2→(4)I9/2 transition of Nd(3+)) and 1000 nm ((2)F5/2→(2)F7/2 transition of Yb(3+)). Singlet oxygen is the key intermediate responsible for the observed CL, which is presumably generated by the reaction of (1)O2 with ligands of the complexes. The CL phenomenon discovered herein paves the way towards the development of lanthanide-based CL probe for (1)O2.

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Dioxirane Oxidations of Compounds other than Alkenes

Adam

Zhao

Kavitha

2009

Oxidation of Organic Compounds by Dioxiranes

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Chemiluminescence in the oxidation of europium β-diketonates by dimethyldioxirane

Cited by 6 publications

References 12 publications

Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

A novel chemiluminescence from the reaction of singlet oxygen with β-diketonates of europium(iii), neodymium(iii) and ytterbium(iii)

Dioxirane Oxidations of Compounds other than Alkenes

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