A coumarin/naphthoquinone monoimine-fused oxazabicyclic derivative was designed, synthesized, and characterized in a one-pot tandem reaction and its fluorescence redox switch properties were investigated. The coumarin emission of the synthesized oxazabicycle is completely quenched by the naphthoquinone monoimine moiety, the corresponding reduced aminonaphthalenol resulted in a moderate increase of the emission intensity. The reduced aminonaphthalenol can be reverted to the original nonfluorescence compound via DDQ oxidation. A reversible, fluorescence switch that can be chemically turned ON and OFF through the control of the redox state of the naphthoquinone monoimine moiety is demonstrated. Copyright ? 2009 The Chemical Society of Japan.
