A highly selective pH switchable colorimetric fluorescent rhodamine functionalized azo-phenol derivative for thorium recognition up to nano molar level in semi-aqueous media: Implication towards multiple logic gates.

Abstract

A new rhodamine functionalized Schiff base (3',6'-bis(diethylamino)-2-((Z)-(5-((E)-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)diazenyl)-2,4-dihydroxybenzylidene) amino)spiro[isoindoline-1,9'-xanthen]-3-one (1) has been synthesized and was characterized spectroscopically. The optical properties of the schiff base have been studied using UV-vis and fluorescence spectra. Schiff base 1 displayed a selective behaviour towards Th4+ ions, as evidenced by UV-vis and fluorescence spectra. It shows visible colour change from orangish-yellow to red upon addition of Th4+ ions. A strong new emission band at 586 nm and about 24-fold enhancement in fluorescence intensity was observed upon binding with Th4+ which could be quenched by subsequent addition of oxalate and chromate ions. Probe 1 also acts as a reversible pH sensor in the highly acidic region (pH < 4, pKa = 2.01) via the photophysical response to pH as well as visible detectable colour change from orangish-yellow to red to pink. The absorbance and emission intensities of 1 diminished in the pH region from 4 to 11.5 and could be recovered by adding acid to adjust the pH < 4. Probe 1 exhibited high binding constant (8.595 × 106 M-1) and low limit of detection (1.122 × 10-9) compared to most previously reported sensors for Th4+ ions. Furthermore, two multiple logic gates i.e. 3 and 5 input, have been constructed.