A Pyrene-Rhodamine FRET couple as a chemosensor for selective detection of picric acid

Abstract

Selective detection of nitroaromatic compounds such as Picric acid (PA), those being explosive materials and hazardous pollutants of environmental and biological concern is highly desirable. With the operational advantages of the chemosensing approach, a pyrene-rhodamine-B couple (1) was explored in this investigation as a ratiometric molecular probe for selective and sensitive detection of picric acid. The bi-fluorophoric probe displayed absorption and fluorescence enhancements along with colourless to reddish-brown colour transition as signaling responses in the selective presence of PA among all the nitro aromatic analyte investigated. The signaling module relies on PA- mediated modulation of various operational photo-physical processes such as (a) inhibition of photo-induced electron transfer (PET) operative from amino-donor to excited pyrene (b) a conformational translation through spiro-ring opening of rhodamine-B segment, and (c) initiation of Fluorescence Resonance Energy Transfer (FRET) between excited pyrene donor and ring-opened rhodamine acceptor. The ratio of fluorescence from both fluorophores (pyrene and Rhodamine) as output channel displayed sensitive signaling performance (LOD = 13.8 nM) in the detection of PA. The investigation that inferred to the PA-induced selectivity in signalling, higher binding affinity (log Ka≈11), a faster response time, and reversibility in signalling with a counter analyte and an operational pH range established the probe’s efficacy as a chemosensor for PA detection.