Four‐membered ring peroxides: 1,2‐dioxetanes and α‐peroxylactones

Adam, Waldemar

doi:10.1002/9780470771730.ch24

Cited by 25 publications

(14 citation statements)

References 298 publications

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“…Also available are compilations and reviews on chemical reactivity and transformation o f excited triplet and singlet species generated in the thermolysis of dioxetanes as exploited for the determination of chemiexcitation yields (Adam. 1982(Adam. , 1983Adam and Cilento, 1983;Adam and Fany, 1985; Adam e t a / .…”

Section: Products (Unimolecular Reaction)mentioning

confidence: 99%

PHOTOCHEMISTRY and PHOTOBIOLOGY WITHOUT LIGHT

Cilento

Adam

1988

Photochem & Photobiology

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Abstract-This review covers the literature since 1980 on chemically and enzymatically generated electronically excited species. The emphasis lies on triplet states of carbonyl products that are derived from dioxetanes and dioxetanones as precursors or from suitable enzymatic oxygenations. Singlet oxygen. an important excited state species in biological processes, is not explicitly treated. The utilization of triplet excited carbonyl products to promote photochemical and photobiological transformations by energy transfer are of primordial interest and not the photomechanistic behavior, photophysical properties and inherent photochemical reactions of such excited state species. Thus, the coverage concentrates on photodamage of DNA and RNA., the photochemistry of favins, vitamin D, tryptophan, arachidonic acid, chlorophyll, lipid peroxidation, urocanase activation, excitation of chlorophlasts, and the aerobic oxidation of Schiff bases derived from amino acids and proteins. The potential perspectives of employing authentic dioxetanes and enzymatically generated dioxetane intermediates as effective photon equivalents in photochemotherapy, phototoxicity, photoaffinity labeling and photogenotoxicity are pointed out, in the hope of stimulating more intensive activity in this emerging and novel bioorganic and photobiological field.

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Section: Products (Unimolecular Reaction)mentioning

confidence: 99%

PHOTOCHEMISTRY and PHOTOBIOLOGY WITHOUT LIGHT

Cilento

Adam

1988

Photochem & Photobiology

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“…High‐energy molecules, 1,2‐dioxetanes, can liberate energy sufficient for the chemiexcitation of a carbonyl fragment during decomposition 1. However, the thermal decomposition of rather simple dioxetanes affords a predominant amount of a triplet‐excited carbonyl compound, along with a small amount of a singlet‐excited carbonyl compound.…”

Section: Intramolecular Charge‐transfer‐induced Chemiluminescence (Ctmentioning

confidence: 99%

“…40 years. However, in the early history of dioxetanes, chemiluminescence could not be compared with bioluminescence with regard to the efficiency of light emission 1–4. The discovery of the intramolecular charge‐transfer‐induced chemiluminescence (CTICL) of dioxetanes in the 1980s by Schaap stimulated the later development of dioxetanes as chemiluminescent compounds 5–7.…”

Section: Introductionmentioning

confidence: 99%

Color modulation for intramolecular charge‐transfer‐induced chemiluminescence of 1,2‐dioxetanes

Matsumoto

Watanabe

Hoshiya

et al. 2008

The Chemical Record

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Dioxetanes bearing an aromatic electron donor decompose with an accompanying emission of light by an intramolecular charge-transfer-induced chemiluminescence (CTICL) mechanism. The color of the chemiluminescence from CTICL-active aryl-substituted dioxetanes is controlled by the design of the aromatic moiety and its substitution pattern, and the substituent on the carbon of the dioxetane ring. In addition to these color modulations, a change in the conformation of dioxetanes bearing a biaryl group was also found to cause a change in the color of CTICL in the coordination sphere of a crown ether complex. This new color modulation system was further developed for optically active dioxetanes bearing 2-hydroxy-1,1'-binaphthyl, the CTICL of which took place under the chiral recognition of optically active crown ether complexes. The spectra of the chemiluminescence from biaryl-type dioxetanes did not coincide with the fluorescence spectrum from the authentic emitter in the coordination sphere, but they did coincide with each other in a completely homogeneous system. This finding suggests that the emitter of CTICL possesses a transient structure, which retains the afterimage of the conformation of the dioxetane.

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“…1,2-Dioxetanes have attracted considerable interest because of the key roles in chemiluminescence and bioluminescence [15,16], which have a broad range of biological, chemical, and medical applications [17,18]. The most common preparation of 1,2-dioxetanes is through the formal [2 + 2] cycloaddition of singlet oxygen ( 1 O 2 ) to electron-rich alkenes [19,20].…”

Section: Introductionmentioning

confidence: 99%