Bicyclic dioxetanes bearing an inden-2-yl or a benzo(b)thiazol-2-yl moiety as a CIEEL-active chemiluminescent substrate emitting red 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 (lambda(max) (CL) = 637 nm). Comparing the chemiluminescent properties for 3 with those for related dioxetane, 1, in which pi-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 (lambda(max) (CL) = 725 nm), though the chemiluminescent efficiency was low.
Watanabe
Nobuko
N
Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, Japan.
Nagamatsu
Kumiko
K
Mizuno
Toshiyuki
T
Matsumoto
Masakatsu
M
D052160:Benzothiazoles; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006573:Heterocyclic Compounds, 1-Ring; D007192:Indenes / Q000737:chemistry*; D008027:Light; D049449:Luminescence; D008163:Luminescent Measurements; D013844:Thiazoles / Q000737:chemistry*
D052160:Benzothiazoles; D001643:Bridged Bicyclo Compounds; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; D007192:Indenes; D013844:Thiazoles; C079142:1,2-dioxetane; C005465:benzothiazole