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
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
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.