The Influence of Substitution on the Formation of Excited Singlet States from the Decomposition of Dioxetanes.
Final technical rept.,
SUSSEX UNIV BRIGHTON (ENGLAND)
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This work was designed to discover whether changes in substitution in dioxetanes would alter the rates of decomposition and the proportion of excited singlet products formed. Thirteen dioxetanes were synthesised and their decomposition studied by monitoring the light emission which accompanied the formation of carbonyl products. It was found that substitution did indeed affect the rate of decomposition, and in the dioxetane derived from benzylidene acridan, remarkably high yields of singlet excited states were obtained. However, it was extremely difficult to produce consistent results, and it was shown that the difficulties were not due to induced decompositon or transition metal catalysis. A very thorough investigation of the effect of solvent was undertaken, incidentally establishing the reliability of the central observations. Highly electron-donating substituents increase the rate of decomposition and that this rate enhancement is accompanied, in one case in particular, by excited singlet yields of about 30.
- Organic Chemistry
- Atomic and Molecular Physics and Spectroscopy