Jy. Chen et Pr. Selvin, Synthesis of 7-amino-4-trifluoromethyl-2-(1H)-quinolinone and its use as an antenna molecule for luminescent europium polyaminocarboxylates chelates, J PHOTOCH A, 135(1), 2000, pp. 27-32
Citations number
21
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
7-Amino-4-trifluoromethyl-2-(1H)-quinolinone (cs124-CF3), has been synthesi
zed and found to be an effective antenna molecule (or sensitizer) for europ
ium, but not terbium, luminescence. Specifically, cs 124-CF3 has been coval
ently attached to the chelates diethylenetriaminepentaacetic acid (DTPA) an
d triethylenepentamine-hexanoic acid (TTHA). When bound to europium, excita
tion in the absorption band (<365 nm) of the cs 124-CF3 leads to characteri
stic europium luminescence: a sharply-spiked emission spectrum, and long-li
ved emission, including 1.19 ms excited-state lifetime for TTKA-CS(CF3)-Eu3
+ and 0.62 ms for DTPA-cs124-CF3-Eu3+. Emission from DTPA-cs124-CF3-Eu3+ (T
THA-CS(CF3)-Eu3+) is about three times (1.7) brighter than that of the non-
fluorinated parent compound, 7-amino-4-methyl-2-(1H)-quinolinone (cs 124),
which we have previously shown to be a valuable lanthanide sensitizer. The
excitation of DTPA-cs124-CF3-Eu3+ is red-shifted approximately 15 nm, enabl
ing excitation at 355 and 365 nm, thereby matching two commonly available e
xcitation sources. The chemical stability of DTPA-cs124-CF3-Eu3+ is also ex
cellent, in contrast to the similar compound, 7-amino-4-trifluoromethyl-2-c
oumarin. It is expected that cs124-CF3 will be a valuable sensitizer for eu
ropium luminescence in time-resolved fluorescence assays, and will also aid
e in the design of future sensitizers. It may also be a useful fluorescent
dye, independent of lanthanides. (C) 2000 Published by Elsevier Science S.A
.