Photoprotodesilylation of 9-trimethylsilylanthracene in alcohols.

It was found that the anomalous fluorescence quenching in methanol (as compared to other solvents) of 9-trimethylsilylanthracene (2) is accompanied by a chemical reaction leading to anthracene. This ipso substitution is due to a hydrogen bonding formation in the excited singlet state preceding the carbon-silicon bond cleavage. The mechanism was studied using stationary and dynamic fluorescence, laser flash photolysis and reactivity kinetics as a function of temperature.