Document Detail


Synthesis of thermally stable acylamino-substituted bicyclic dioxetanes and their base-induced chemiluminescent decomposition.
MedLine Citation:
PMID:  20681740     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Nobuko Watanabe; Yusuke Sano; Haruna Suzuki; Masatoshi Tanimura; Hisako K Ijuin; Masakatsu Matsumoto
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-08-27     Completed Date:  2010-12-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5920-6     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293 Japan.
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MeSH Terms
Descriptor/Qualifier:
Bicyclo Compounds, Heterocyclic / chemical synthesis*,  chemistry
Chemiluminescent Measurements
Heterocyclic Compounds / chemical synthesis*,  chemistry
Molecular Structure
Stereoisomerism
Temperature*
Chemical
Reg. No./Substance:
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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