| Project/Area Number |
13640546
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kanagawa University |
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Principal Investigator |
WATANABE Nobuko Kanagawa University, Faculty of Science, Assistant Professor, 理学部, 助手 (40291744)
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| Co-Investigator(Kenkyū-buntansha) |
MATSUMOTO Masakatsu Kanagawa University, Faculty of Science, Professor, 理学部, 教授 (10260986)
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| Project Period (FY) |
2001 – 2002
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| Project Status |
Completed (Fiscal Year 2002)
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| Budget Amount *help |
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 2002: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2001: ¥1,300,000 (Direct Cost: ¥1,300,000)
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| Keywords | Chemiluminescence / CIEEL / 1,2-Dioxetane / Long-wavelength light / 1.2-ジオキセタン / 発光種 / ナフタレン環 |
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| Research Abstract |
Dioxetanes having an electron-donor decompose to emit light effectively by the CIEEL (chemically initiated electron exchange luminescence) mechanism. Thus, the CIEEL-active dioxetanes would be a promising entry to a variety of chemiluminescent substrates.
In this work, we investigated design and synthesis of new CIEEL-active dioxetanes emitting a long-wavelength light (crimson light).
1) 5-t-Butyl-1-[(t-butyldimethylsiloxy)benzothiazol-2-yl]-4, 4-dimethyl-2, 6, 7-trioxabicyclo[3. 3. 0]-heptane emitted crimson light (maximum wavelength = 730nm).
2) Dioxetanes substituted with 3-oxyphenyl bearing an aryl substituent at the 4- or 5-position emitted light with maximum wavelength longer than that for 3-oxyphenyl-substituted dioxetane. Among these dioxetanes, 4-azolylphenyl-substituted dioxetanes emitted light effectively also in aqueous media.
3) New CIEEL-active dioxetanes, 5-aryl-1-t-butyl-4, 4-dimethyl-2, 6, 7-trioxabicyclo[3. 2. 0] heptanes, which afford an aromatic ketone as an emitter, were synthesized and found to emitt light with maximum wavelength longer than the corresponding 5-aryl-1-t-butyl isomers.
4) A3-(cyanomethyl)phenyl-substituted dioxetane emitted crimson light (maximum wavelength = 702nm). This new type dioxetane decomposed through an intermediary dioxetane bearing a benzylic carbanion.
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