Organic superbase-induced chemiluminescent decomposition of a hydroxyaryl-substituted dioxetane: Unique effect of a bifunctional guanidine base on the chemiluminescence profile of a bicyclic dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety

• Published in: Tetrahedron letters 2018-03, Vol.59 (11), p.971-977
• Main Authors: Watanabe, Nobuko, Wakatsuki, Ayu, Ijuin, Hisako K., Kabe, Yoshio, Matsumoto, Masakatsu
• Format: Article
• Language: English
• Subjects: Bifunctional guanidine base; Chemiluminescence; Dioxetane; Superbase
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2018.01.045

[Display omitted] •Superbases effectively induced chemiluminescence from hydroxyaryl-dioxetanes.•TBD exhibited unique effect on chemiluminescent decomposition.•The unique effects of TBD may be attributed to its bifunctional character. Organic superbases represented by TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) effectively induced the decomposition of hydroxyaryl-substituted dioxetanes in acetonitrile to give bright light. The color of the chemiluminescence from a dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety varied depending on the base used. In addition to this change in the color of emission, TBD increased the chemiluminescence efficiency 2- to 5-fold compared to the results with other base systems and accelerated decomposition of the dioxetane. These unique effects of TBD may be due to its “bifunctional” character, which is different from those of other organic superbases. Chemiluminescent decomposition of the dioxetane was effectively induced by superbases even in apolar p-xylene.