Design and synthesis of chemiluminescent substrates with high luminescent efficiency in an aqueous system: 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes bearing a 3-hydroxy-4-(1-iminoethyl)phenyl moiety at the 1-position.
A CIEEL-active dioxetane bearing a 4-acetyl-3-hydroxyphenyl moiety has very recently been found to emit light effectively, even in an aqueous system, albeit with a very slow CIEEL decay rate. As an attempt to improve the CIEEL decay rate of this type of dioxetane, three dioxetanes, in which a carbonyl in the 4-acetyl-3-hydroxyphenyl moiety was modified into an oxime, oxime O-methyl ether, or semicarbazone, were synthesized. These three dioxetanes decomposed to emit light far more rapidly than the parent 4-acetyl-3-hydroxyphenyl-substituted dioxetane. Among them, a dioxetane bearing a 3-hydroxy-4-(1-methoxyiminoethyl) phenyl, namely an oxime O-methyl ether derivative, gave high chemiluminescent efficiency. As for a semicarbazone derivative, decrease of the chemiluminescent yield was minimal, even in an aqueous system.
Matsumoto
M
M
Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1205, Japan.
Sakuma
T
T
Watanabe
N
N
D000097:Acetonitriles / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000378:metabolism; D006573:Heterocyclic Compounds, 1-Ring; D008163:Luminescent Measurements; D012664:Semicarbazones / Q000737:chemistry / Q000378:metabolism; D012680:Sensitivity and Specificity; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D014867:Water / Q000494:pharmacology
D000097:Acetonitriles; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; D012664:Semicarbazones; D014867:Water; C079142:1,2-dioxetane; C032159:acetonitrile