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 the1-position

Citation
M. Matsumoto et al., 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 the1-position, LUMINESCENC, 16(4), 2001, pp. 275-280
Citations number
5
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Biochemistry & Biophysics
Journal title
LUMINESCENCE
ISSN journal
1522-7235 → ACNP
Volume
16
Issue
4
Year of publication
2001
Pages
275 - 280
Database
ISI
SICI code
1522-7235(200107/08)16:4<275:DASOCS>2.0.ZU;2-#
Abstract
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 CIEE L decay rate of this type of dioxetane, three dioxetanes, in which a carbon yl 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-hydro xyphenyl-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 syst em. Copyright (C) 2001 John Wiley & Sons, Ltd.