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Chemiluminescence of bicyclic dioxetanes bearing a hydroxyphenyl moiety substituted with carbazolyl, indolyl or benzotriazolyl group in the coordination sphere
Author(s) -
Matsumoto Masakatsu,
Yamada Kazutaka,
Watanabe Nobuko,
Ijuin Hisako K.
Publication year - 2007
Publication title -
luminescence
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.428
H-Index - 45
eISSN - 1522-7243
pISSN - 1522-7235
DOI - 10.1002/bio.980
Subject(s) - dioxetane , chemistry , chemiluminescence , moiety , ether , medicinal chemistry , photochemistry , bicyclic molecule , crown ether , stereochemistry , organic chemistry , ion
Bicyclic dioxetanes bearing a 3‐(carbazol‐9‐yl)‐5‐hydroxyphenyl 2a , 3‐hydroxy‐5‐(indol‐1‐yl)phenyl 2b , or 3‐(benzotriazol‐1‐yl)‐5‐hydroxyphenyl group 2c were synthesized. Base‐induced decomposition of dioxetane 2a displayed intense light, the maximum wavelength ( λ max CTICL ) of which changed depending on the crown ether complex of potassium t‐ butoxide used as a base, although the magnitude of λ max CTICL change was considerably smaller than the case of dioxetane bearing a 3‐(anthracen‐9‐yl)‐5‐hydroxyphenyl group 1 . Chemiluminescence (CL) from 2b resembled closely that from 2a in response to the crown ether complexes. On the other hand, dioxetane 2c exhibited emission of red light on treatment with tetrabutylammonium fluoride. The colour of light changed significantly and exhibited two peaks in the CL spectrum when treated with complex of bulky dibenzyldiazacrown ether 13 . Copyright © 2007 John Wiley & Sons, Ltd.