1,2-dioxetane

The chemical substance 1,2-dioxetane (systematically named 1,2-dioxacyclobutane, also known as ethylene peroxide or peroxyethane) is a heterocyclic, organic compound with formula , containing a ring of two adjacent oxygen atoms and two adjacent carbon atoms. It is therefore an organic peroxide, and can be viewed as a dimer of formaldehyde ().

Chemical data

Formula: C2H4O2
Molecular weight: 60.05 g/mol
IUPAC name: dioxetane
SMILES: C1COO1
InChIKey: BVTJGGGYKAMDBN-UHFFFAOYSA-N
XLogP: -0.1
Polar surface area: 18.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

296 papers

Energy Transfer Chemiluminescent Spiroadamantane 1,2-Dioxetane Probes for Bioanalyte Detection and Imaging.Angewandte Chemie (International ed. in English) · 2022
Chemiluminescent Probes Based on 1,2-Dioxetane Structures For Bioimaging.Chemistry, an Asian journal · 2022
Phenoxy-1,2-dioxetane-based activatable chemiluminescent probes: tuning of photophysical properties for tracing enzymatic activities in living cells.The Analyst · 2024
Chemiluminescent 1,2-Dioxetane Iridium Complexes for Near-Infrared Oxygen Sensing.Angewandte Chemie (International ed. in English) · 2022
Sensitive detection of fluid biomarkers using adamantylidene 1,2-dioxetane based chemiluminescent probes.Chemical communications (Cambridge, England) · 2025

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Wikidata facts

Mass: 60.021

Show 3 more facts

Commons category: 1,2-Dioxetane
chemical formula: C₂H₄O₂
canonical SMILES: C1COO1

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Luminescence
Derivatives
Carbon monoxide generation
See also
References

== Luminescence == Chemiluminescence was first observed with lophine (triphenylimidazole). When in basic solution, this compound converts to the imidazolate, which reacts with oxygen to eventually give the 1,2-dioxetane. Fragmentation of the dioxetane gives the excited state of an anionic diamide.

Excerpted from Wikipedia’s “1,2-dioxetane” article, available under the CC BY-SA 4.0 licence.