Abstract

The anion binding property of a series of easily synthesizable, isonicotine acid hydrazide based optical switches were studied in the semi-aqueous environment. Irrespective to the position of the hydrazide units, all three compounds show color change (as well as turn-off fluorescence response) with CN− ion, presumably due to hydrogen bonding triggered intramolecular charge transfer interaction. The compound with phenanthroline as the signaling unit, shows effective E Z isomerization with substantial amount of kinetically stable Z-isomer in the equilibrium, stabilized by intramolecular hydrogen bonding. This compound showed a 1:1 binding interaction with CN− ion due to its ‘U’ shaped conformation. On the other hand, compound with two isoniazid hydrazide moieties at 1,4-positions, shows 1:2 interaction with CN− ions. Further, the probe molecules were utilized for the detection of CN− ions in water samples collected from different natural resources. Low-cost portable optical kit based on reusable paper strips were designed for rapid, on-location detection purpose.

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