Design, Synthesis and Photochemical Properties of a Phenalenone-Based pH Sensor: Switchable pH Sensing in Four...

The synthesis and pH-sensing property of a novel phenalenone-based compound, 9-(4-hydroxyphenylamino)-1-oxo-phenalenone (HPAP), is reported. The newly synthesized compound is capable of functioning as a pH sensor in the region of pH 7 to 12. The sensor can be used as a colorimetric indicator in the transition from pH 10 to pH 11. The sensor is able to function in four detectable channels. All four channels (UV, emission, colorimetric/visible and photoluminescence) have been shown to be reversible, thus implying the reuse of this single-molecule sensor and indicator for several experiments. Mechanistic investigations have been performed by UV, NMR and DFT studies which indicate that a photoinduced electron transfer (PET) based mechanism could be operative. Straightforward and cost-effective application of the sensor in thin-layer chromatography has also been established.