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Achieving selective detection of target analytes in aqueous media continues to be an arduous proposition. Herein, we report the conceptualization and synthesis of a novel tailor-fit molecular probe R based on 1,8-naphthalimide which acts as a trifunctional molecular sensor for CN - , Fe 3+ and H 2 S. R shows colorimetric and fluorometric "on-off" relay recognition for CN - (red colour and orange emission) and Fe 3+ (no colour and no emission) in 5% H 2 O + DMSO medium which is experimentally ascertained to be a tandem deprotonation-protonation process and is supported by 1 H-NMR titration. Among all RSS (Reactive Sulphur Species), R shows selectivity for H 2 S through red colouration. Other coexistent anions, cations and RSS cause no discernible perturbation to the detection process. The detection of H 2 S is attributed to a chemodosimetric reduction of the nitro to amino group as evidenced by a potentiometric titration assay. The experimental observations are well supported by DFT theoretical calculation. The K  a for CN - /Fe 3+ are 1.4 × 10 4 M -1 , 6.07 × 10 4 M -1 respectively and photochemical yield of R + CN - is 0.86. Limit of detections for CN - , Fe 3+ and H 2 S are 17.5 nM, 8.69 μM and 8.1 μM respectively. Receptor R is effective for real time applications, bio-compatible and has been successfully employed for confocal fluorescence imaging of RAW264.7 cell and zebrafish.

rsc advances

Naphthalimide based smart sensor for CN−/Fe3+ and H2S. Synthesis and application in RAW264.7 cells and zebrafish imaging