Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system

The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemilumi...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 9; pp. 1644 - 1647
Main Authors Watanabe, Nobuko, Oguri, Azusa, Horikoshi, Miho, Takatsuka, Hikaru, Ijuin, Hisako K., Matsumoto, Masakatsu
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 26.02.2014
Subjects
Aqueous system
Chemiexcitation efficiency
Chemiluminescence
Decomposition
Dioxetane
Emitters
Fluorescence
Solvents
Tetrahedrons
Chemiexcitation efficiency
Aqueous system
Chemiluminescence
Dioxetane
Online AccessGet full text

Cover

More Information
Summary:The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemiluminescence efficiency in NaOH/H2O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H2O, and estimated that the singlet-chemiexcitation efficiency ΦS was 6.1×10−3 for the decomposition of B in NaOH/H2O. On the other hand, ΦS for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.089