Synthesis and chemiluminescent decomposition of spiro[1, 2-dioxetane-3,6'-benzo(c)chromene]s.
Two spiro[1,2-dioxetane-3,6'-benzo(c)chromene]s bearing a t-butyldimethylsiloxy as a trigger at the 10'- or 2'-position were synthesized. On treatment with tetrabutylammonium fluoride in DMSO at 25 degrees C, the 10'-siloxyspiro[1,2-dioxetane-3, 6'-benzo(c)chromene] decomposed rapidly to afford a flash of blue light. The CIEEL decay of this spirochromenedioxetane was also induced by basic silica gel in hexane. By contrast, TBAF-induced decomposition of an analogous spiro[1,2-dioxetane-3, 6'-benzo(c)chromene] with a trigger at the 2'-position, resulted in emission of yellow light with very low efficiency.
Matsumoto
M
M
Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-12, Japan.
Kawahara
M
M
Watanabe
N
N
D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring; D008163:Luminescent Measurements; D013057:Spectrum Analysis; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001578:Benzopyrans; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; D013141:Spiro Compounds; C079142:1,2-dioxetane