A naphthalimide functionalized fluoran with AIE effect for ratiometric sensing Hg²⁺ and cell imaging application

The pollution caused by mercury ions (Hg²⁺) poses a potential threat to public health. Therefore, monitoring Hg²⁺ concentration in the environment is necessary and significant. In this work, a naphthalimide functionalized fluoran dye NAF has been prepared, which shows a new red-shift in emission at 550 nm with the maximum intensity in a mixture of water-CH₃CN (v/v = 7/3) due to aggregating induced emission (AIE) effect. Meanwhile, NAF can be employed as a Hg²⁺ ions sensor, which displays a selective and sensitive response to Hg²⁺ ions by the reduced fluorescence of naphthalimide fluorophore and increased fluorescence of fluoran group, respectively, showing ratiometric fluorescence signal changes with more than 65-fold emission intensity ratio increase and naked eyes visible color change. In addition, the response time is fast (within 1 min) and the sensing can be conducted in a wide pH range (4.0-9.0). Moreover, the detection limit has been evaluated to be 5.5 nM. The sensing mechanism may be attributed to the formation of a π-extended conjugated system due to the Hg²⁺ ions-induced conversion of spironolactone to the ring-opened form, partially accompanied by the fluorescence resonance energy transfer (FRET) process. Significantly, NAF exhibits suitable cytotoxicity to living HeLa cells, which allows it to be utilized for ratiometric imaging of Hg²⁺ ions assisted by confocal fluorescence imaging.