Two new chemosensors 1 and 2 derived from 5,12- and 5,7-dioxocyclams were prepared and their signaling behaviors toward transition metal ions were investigated. Chemosensors 1 and 2 showed very efficient responses toward $Cu_{2+}$ and $Hg_{2+}$ ions. Ratiometric analysis of the fluorescence changes in pyrene monomer and excimer emissions clearly demonstrated the $Cu_{2+}$- and $Hg_{2+}$-selective signaling behavior. The signaling mechanism of the chemosensors is due to conformation changes upon complexation with metal ions and the inherent quenching nature of the complexed $Cu_{2+}$ and $Hg_{2+}$ ions themselves.