Journal
TETRAHEDRON
Volume 68, Issue 30, Pages 6079-6087Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.078
Keywords
Dioxetane; Chemiluminescence; Charge-transfer-induced decomposition; Fluorescein
Categories
Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [17550050, 21550052]
- Grants-in-Aid for Scientific Research [22550046, 21550052, 17550050] Funding Source: KAKEN
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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 Phi(CL) 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 Phi(CL) was hardly observed by the simple addition of 25 or 26 as a model of a tethered fluorescer. (C) 2012 Elsevier Ltd. All rights reserved.
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