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Cited by 68bioluminescence and chemiluminescence researchLuminescence and Fluorescent MaterialsEnergetic Materials and Combustion

Four‐membered cyclic peroxides: Carriers of chemical energy

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Bastos, Erick Leite, Farahani, Pooria, Bechara, Etelvino J.H., Baader, Wilhelm Josef·2017·Journal of Physical Organic Chemistry
DOI 10.1002/poc.3725
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Abstract

Four‐membered cyclic peroxides are high‐energy compounds often associated to cold light emission, but whose chemical and biological roles are still matters of debate. The often‐dangerous synthesis of 1,2‐dioxetanes, achieved around 50 years ago, has been mastered over the years to a point where some derivatives are commercially available. This fact does not imply that 1,2‐dioxetanes can be conveniently prepared in the gram scale or that the synthesis of analogous 1,2‐dioxetanones and the elusive 1,2‐dioxetanedione are simple. Important questions on the mechanism of chemiluminescence and bioluminescence reactions are under experimental and theoretical scrutiny. The available data have contributed to relate structural and medium effects to the quantum efficiency of these compounds to produce excited states. Consequently, such peroxides have been suggested to produce biologically relevant electronically excited species in vivo in the absence of light. The connection of this hypothesis with melanin‐mediated photodamage in the dark has renewed the interest in such cyclic peroxides. This review gives some insight on the synthesis, chemiluminescence mechanism, and biological relevance of 1,2‐dioxetanes, 1,2‐dioxetanones, and 1,2‐dioxetanedione and provides practical protocols for those interested in engaging this field.

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Authors
Bastos, E. L., Farahani, P., Bechara, E. J. H., & Baader, W. J.
Affiliations
Universidade de São Paulo (BR)
Corresponding author
  • Bastos, Erick Leite
  • Baader, Wilhelm Josef
ORCID
Venue
Journal of Physical Organic Chemistry
Publisher
Wiley
Published
2017-06-19
Volume
30
Issue
9
ISSN
  • 0894-3230 (ISSN-L)
  • 1099-1395
DOI
10.1002/poc.3725
OpenAlex
W2643027341
Cited by
68
References
227
Citations by year
2026: 5 · 2025: 4 · 2024: 8 · 2023: 9 · 2022: 9 · 2021: 10 · 2020: 8 · 2019: 6 · 2018: 8 · 2017: 1
FWCI
2.57
Type
journal article
Language
en
Open access
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
Journal of Physical Organic Chemistry (publishedVersion)
Funders
  • Fundação de Amparo à Pesquisa do Estado de São Paulo (2014/22136‐4, 2015/02314‐8, 2016/21445‐9)
  • Conselho Nacional de Desenvolvimento Científico e Tecnológico (Productivity fellowships for ELB and EJHB)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › bioluminescence and chemiluminescence research
  • Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
  • Physical Sciences › Engineering › Mechanics of Materials › Energetic Materials and Combustion
Keywords
1,2-dioxetanes, chemiluminescence, bioluminescence, chemiluminescence mechanism, quantum efficiency, excited states, chemical energy carriers

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