Optical Sensing of Cesium Using 1,3-Alternate Calix[4]-mono- and Di(anthrylmethyl)aza-crown-6

We have synthesized two derivatives of alkylanthracene covalently bonded to 1,3-alternate calix4]aza-crown-6 at the nitrogen position to study the effect of alkali metal ion complexation on the emission properties of anthracene fluorophore. The mono- and dianthryl-substituted probes are weakly fluorescent because their emission is partially quenched by photoinduced electron transfer (PET) from the nitrogen lone pair to the excited singlet state of anthracene. Upon complexation of alkali metal ions (e.g. K⁺, Cs⁺) by the crown moiety, the nitrogen lone pair can no longer participate in the PET process causing an enhancement in the emission of anthracene fluorophore (fluorescent turn on). The maximum fluorescence enhancement observed upon complexation of cesium ions by mono- and dianthryl-substituted calix4]aza-crown-6 relative to the uncomplexed form was 8.5- and 11.6-fold, respectively.