Precisely designed NIR based conjugated framework as a solid state emitter for selective recognition of cyanide ion in solid state and cancer cells

Abstract

Cyanide is undoubtedly dangerous and fast acting chemical employed in various industrial applications with toxic side effects, which raises urgent need for its monitoring. In this context, oxazolonaphthoimidazo[1,2-a]pyridine-malononitrile (ONIM) conjugate linked by vinyl linkage was designed, synthesized and characterised by FT-IR, NMR and mass spectrometry. The developed probe has been evaluated for the colorimetric and fluorometric detection of cyanide ion. An obvious color change with unique rapid “turn-off” fluorometric response was observed within 5 s upon addition of CN– thus reflecting its better acuteness and sensitivity over other competing anions. The developed probe exhibits a detection limit of 9.54 nM which is very low in comparison to maximum permitable amount of cyanide in drinking water (1.9 µM). The probe is stable within the pH range of 2–9 and suitable for the recognition of CN– in the pH range of 7 to 10, specially at neutral pH conditions. The chemodosimetric approach based detection mechanism was authenticated by 1H NMR titration and DFT calculations. The solid state applications were established by utilising ONIM impregnated TLC plates and filter paper in cyanide recognition. The solid state emissive behaviour of ONIM offers on-spot detection of the cyanide anion. Additionally, the practicability of ONIM has been extended in live cell imaging of CN– in human breast cancer cell (MDA-MB-231), which revealed a “turn-off” fluorescence response for the probe in the presence of CN– ion.