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UBC Theses and Dissertations

Chemiluminescence of indolyl peroxides Chang, Yew Chun


Indolyl hydroperoxides have been discovered to be chemiluminescent in presence of potassium t-butoxide in dimethyl sulphoxide. A number of derivatives of indole and the corresponding peroxide have been prepared in an effort to elucidate the mechanism of chemiluminescence of this class of compound. The chemiluminescent reaction of two of the brightest hydroperoxides (X11A and XV111A) yielded a major product, the amides (Xlla and XVllla), in about 70% yield. The emitter has been identified as the amide product based on spectroscopic data. It was found that electron-donating substituents enhance the chemiluminescence intensity. A study of 2-(p-phenyl) substituted indolyl hydroperoxides shows a Hammett correlation with δ for 7 of the compounds. The chemiluminescence of compounds (XllA and (XV111A) shows a pseudo first order dependence on the concentration of (X11A and XV111A) (in excess base). Energy transfer has been observed to occur in the thermochemiluminescence of 11-tetrahydroperoxyindolenine (XXVA).

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