Abstract
4‐Ferrocenyl‐6,7‐dimethoxy‐3,4‐dihydrocoumarin (3) was synthesized by intermolecular hydroarylation of phenol from β‐ferrocene acrylic acid, and structure has been thoroughly characterized and confirmed by analysing X‐ray single‐crystal data. Compound 3 serves as highly selective fluorescent probe towards explosive picric acid (PA) through quenching of fluorescence in aqueous media. Probe 3 ensures high selectivity for PA in the background presence of various nitroaromatics, anions, cations and some phenols. The LoD for PA has been estimated to be 25.0 ppb using fluorescent probe 3. Binding stoichiometry and binding site of 3 towards PA have been supported by Job's plot, ESI‐mass, performing NMR titration and eventually by developing a model compound 4‐ferrocenyl‐3,4‐dihydrocoumarin 4, which strongly suggested 6,7‐dimethoxy groups as best probable binding site for PA. Overall, present approach deals with development of a ferrocenyl‐dihydrocoumarin conjugate for highly selective and ultrasensitive ‘turn‐off’ fluorescent probe for PA, which has been well‐supported through rational spectral analyses as well as through synthesizing a model compound.
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