Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
Volume 218, Issue 1, Pages 41-47Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jphotochem.2010.12.001
Keywords
Chemiluminescence; 1,2-Dioxetane; Fenchyl group; Organic peroxides; Intramolecular CIEEL
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Funding
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)
- Arbeitsgemeinschaft industrieller Forschungsvereinigungen Otto von Guericke e.V. (AiF)
- Deutscher Akademischer Austauschdienst (DAAD)
- Coordenadoria de Aperfeicoamento de Pessoal de Ensino Superior (CAPES) [BEX 1132/04-0]
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The synthesis and study of the chemiluminescence parameters and thermal stability of 1,2-dioxetanes containing a spirofenchyl substituent are reported. Three fenchyl-substituted 1,2-dioxetanes were synthesized by photooxygenation of the corresponding alkenes, obtained by Barton-Kellogg olefination of the readily available (-)-fenchone. The fenchyl-substituted 1,2-dioxetanes showed thermal stabilities similar to those of the corresponding spiroadamantyl-substituted derivatives, although being slightly more labile with respect to unimolecular decomposition than the latter derivatives, which are widely utilized as labels in a great variety of chemiluminescent immunoassays. Fluoride induced decomposition of one triggerable fenchyl 1,2-dioxetane derivative showed kinetic parameters similar to those of the corresponding adamantyl-substituted derivative. The chemiluminescence quantum yields in the one percent range are also similar to that of other widely utilized chemiluminescence systems as the luminol reaction. These results indicate that fenchyl-substituted 1,2-dioxetanes can potentially be utilized as a cheaper alternative to substitute the corresponding spiroadamantyl derivatives in bioanalytical applications. (C) 2010 Elsevier B.V. All rights reserved.
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