Synthesis of bicyclic dioxetanes tethering a fluororescer through an ω-carbamoyl-substituted linker and their high-performance chemiluminescence in an aqueous system

Bicyclic dioxetanes 3 and 4 tethering a fluorescein or 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety through a linker were synthesized by the use of dihydrofuran-intermediate 5 or its advanced intermediate 6. These dioxetanes underwent base-induced decomposition to effectively give light due to intra...

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Veröffentlicht in:Tetrahedron 2012-07, Vol.68 (30), p.6079-6087
Hauptverfasser: Watanabe, Nobuko, Kino, Hidetoshi, Watanabe, Shinichiro, Ijuin, Hisako K., Yamada, Masashi, Matsumoto, Masakatsu
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Sprache:eng
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Zusammenfassung:Bicyclic dioxetanes 3 and 4 tethering a fluorescein or 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety through a linker were synthesized by the use of dihydrofuran-intermediate 5 or its advanced intermediate 6. These dioxetanes underwent base-induced decomposition to effectively give light due to intramolecular energy-transfer from an excited oxidobenzoate to a tethered fluorophore. Although the chemiluminescence efficiency ΦCL values for 3 and 4 were only ca. 2-fold greater than that for parent 2 in a TBAF/acetonitrile system, these values were 30–550-fold greater than that for 2 in a NaOH/H2O system. Such marked increase of ΦCL was hardly observed by the simple addition of 25 or 26 as a model of a tethered fluorescer. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.04.078