| Synthesis of thermally stable acylamino-substituted bicyclic dioxetanes and their base-induced chemiluminescent decomposition. | |
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MedLine Citation:
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PMID: 20681740 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Hydroxyaryl-substituted dioxetanes 2-4 fused with a pyrrolidine ring were selectively synthesized by singlet oxygenation of the corresponding dihydropyrroles 5-7. These N-acylamino-substituted bicyclic dioxetanes were quite stable thermally, and 2a and 2b were estimated to possess half-lives of 32 and 34 y at 25 degrees C. When treated with TBAF (tetrabutylammonium fluoride) in DMSO, these dioxetanes underwent charge-transfer-induced decomposition (CTID) to emit yellow-orange light. The chemiluminescence efficiencies Phi(CL) for dioxetanes 2 ranged from 10(-6) to 10(-2). On the other hand, dioxetane 4 bearing a 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety showed chemiluminescent decomposition with high efficiency (Phi(CL) = 0.15) comparable to its oxy-analogue 26. Prominent characteristics for CTID of the present dioxetanes were that the N-acylamino-group influenced the color of chemiluminescence as well as the rate of decomposition k(CTID), and furthermore an N-acyl substituent could decisively affect the singlet-chemiexcitation efficiency, as observed for the case of 2b. |
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Authors:
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Nobuko Watanabe; Yusuke Sano; Haruna Suzuki; Masatoshi Tanimura; Hisako K Ijuin; Masakatsu Matsumoto |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Sep |
Date Detail:
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Created Date: 2010-08-27 Completed Date: 2010-12-08 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5920-6 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293 Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Bicyclo Compounds, Heterocyclic
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chemical synthesis*,
chemistry Chemiluminescent Measurements Heterocyclic Compounds / chemical synthesis*, chemistry Molecular Structure Stereoisomerism Temperature* |
| Chemical | |
Reg. No./Substance:
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0/Bicyclo Compounds, Heterocyclic; 0/Heterocyclic Compounds; 6788-84-7/1,2-dioxetane |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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