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Fluorescence Quenching and Photoreactions of 2,3-Diazabicyclooct-2-enes. A Case of Charge Transfer and Hydrogen Atom Transfer
Engel, Paul S.,Kitamura, Akihide,Keys, Dalen E.
, p. 5015 - 5021 (2007/10/02)
A variety of organic compounds have been found to quench the long-lived fluorescence of 2,3-diazabicyclooct-2-ene (DBO), but photochemical reactions take place only with good hydrogen atom donors and tetrahalomethanes.A hydrogen isotope effect on kq of 1.7-3.0 was observed with 1,3- and 1,4-cyclohexadiene.While both quenchers photoreduced DBO, the 1,3-isomer also dimerized to a mixture characteristic of triplet diene.The results are rationalized in terms of the usual encounter complex and ion pair except that the former can undergo hydrogen transfer or react with 1,3-cyclohexadiene.A second case of photochemically induced electron transfer fragmentation was found in the reaction of 1-phenyl-DBO with bromotrichloromethane.
