Synthesis of a Bicyclic Dioxetane Substituted with 3 - (Acetylsulfanyl) - Phenyl Group and Its Base-induced Chemiluminescent Decomposition
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Bicyclic dioxetane bearing a 3-(acetylsulfanyl)phenyl group, 1-[3-acetylsulfanyl)phenyl]-5-tert-butyl-4,4-dimethyl-2-oxabicyclo[3.2.0]heptane, was synthesized from the corresponding aryl-substituted dihydrofuran by means of singlet oxygenation. When this dioxetane was treated with potassium tert-butoxide in DMSO, it decomposed rapidly to emit yellow light with moderate chemiluminescence efficiency (ca 0.2 %). The singlet chemiexcitationefficiency was estimated to be more than 10 %. The dioxetane was found to displaychemiluminescence with accompanied by considerable solvatochromism: lmaxCL = 538 nm in DMSO, but 570-595 nm in H2O.
- 神奈川大学の論文
- 2009-06-30
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