Bicyclic dioxetanes bearing an inden-2-yl or a benzo(b)thiazol-2-yl moiety as a CIEEL-active chemiluminescent substrate emitting red light
Version of Record online: 31 MAR 2005
Copyright © 2005 John Wiley & Sons, Ltd.
Volume 20, Issue 2, pages 63–72, March/April 2005
How to Cite
Watanabe, N., Nagamatsu, K., Mizuno, T. and Matsumoto, M. (2005), Bicyclic dioxetanes bearing an inden-2-yl or a benzo(b)thiazol-2-yl moiety as a CIEEL-active chemiluminescent substrate emitting red light. Luminescence, 20: 63–72. doi: 10.1002/bio.799
- Issue online: 31 MAR 2005
- Version of Record online: 31 MAR 2005
- Manuscript Accepted: 29 OCT 2004
- Manuscript Received: 25 SEP 2004
- Ministry of Education, Science, Sports and Culture, Japan.
- CIEEL-active 1,2-dioxetane;
- crimson light
Bicyclic dioxetanes bearing 5-(t-butyldimethylsiloxy)inden-2-yl, 3, or 5-(t-butyldimethylsiloxy)benzo(b)thiazol-2-yl, 4, were synthesized. On treatment with large excess of tetrabutylammonium fluoride in DMSO, dioxetane, 3, decomposed rapidly with accompanying emission of red (vermilion) light (λmaxCL = 637 nm). Comparing the chemiluminescent properties for 3 with those for related dioxetane, 1, in which π-conjugation system is not fixed in plane, both CIEEL-decay rate and chemiluminescent efficiency were found to be improved for 3. Chemiluminescent decomposition of dioxetane, 4, was similarly induced to emit crimson light (λmaxCL = 725 nm), though the chemiluminescent efficiency was low. Copyright © 2005 John Wiley & Sons, Ltd.