Nonpolar selective emission (NPSE) of carbonyl-bridged rhodols

Polarity-responsive luminophores (PRLs), whose emission properties change in response to the polarity of the surrounding environment, are used for the fluorescence sensing of intracellular environments and various chemical compounds. Herein, we propose a concept called nonpolar selective emission (NPSE) for the development of a new PRL family. Unlike the conventional emission of PRLs, the NPSE luminophore can switch to a completely non-emissive state upon a slight increase in solvent polarity. The NPSE concept offers a new means of distinguishing between nonpolar and low-polarity environments. Moreover, the NPSE property is little affected by the viscosity of the surrounding medium. We demonstrate that NPSE dyes can be used as emission sensors for molecular gases. Furthermore, we discovered the potential use of NPSE dyes as a time-dependent security ink triggered by the volatilization of polar molecules.