Chemiluminescence of bicyclic dioxetanes bearing a hydroxyphenyl moiety substituted with carbazolyl, indolyl or benzotriazolyl group in the coordination sphere

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 (lambda(CTICL)(max))of which changed depending on the crown ether complex of potassium t-butoxide used as a base, although the magnitude of lambda(CTICL)(max) change was considerably smaller than the case of dioxetane bearing a 3-(anthracen-9yl)-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 (C) 2007 John Wiley & Sons, Ltd.