| Research Abstract |
1. Design of Thermally Stable Dioxetanes : Bicyclic dioxetanes, 5-Alkyl-1-aryl-4,4-dimethyl-2-oxabicyclo[3.2.O]heptanes were synthesized. Among them, dioxetanes bearing a 5-tert-butyl were found to possess marked thermal stability. Even dioxetanes fused with six-membered ring, which have been reported to be in general far less stable than their five-membered ring analogs, were found to become very stable thermally by means of 3,3-steric interaction.
2. Design of New Triggering System : By deprotonation or deprotection (triggering), a dioxetane bearing a phenolic group produce an unstable dioxetane bearing an oxyphenyl anion, which decomposes rapidly to emit light by intramolecular charge transfer mechanism where an oxyphenyl anion acts as an electron donor. An anion of m-aminophenyl group acts also as an aromatic electron donor other than phenolic moiety to induce decomposition of a dioxetane to emit flash red light.
3. Design of Fluorophore : Six dioxetanes bearing a 2-naphthyl with a tert-butyldimethylsiloxy at the various position were synthesized and their fluoride-induced chemiluminescent decomposition was examined. Naphthyl-substituted dioxetanes having a trigger (siloxy) at the 5-, 7-, or 8-position emitted red light, while their analogs with a trigger at the 3- or 6-position afforded flash blue light. Dioxetanes bearing a benzofuran, benzothiophene, or benzothiazole were also synthesized.
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