Antharacene-modified isophorone derivative with NIR-emission for hypochlorite detection by the oxidative decomposition reaction and its applications

Abstract

The excess level of hypochlorite may pose a significant problem for living organisms and environment. Therefore, the development of sensitive, reliable and facile-to-apply sensing molecules for hypochlorite detection is essential. The present work reports a novel antharacene-modified isophorone (IMA) fluorescent sensor as a detecting material for toxic and corrosive hypochlorite. IMA demonstrates excellent selectivity toward hypochlorite over other competing analytes through a distinct fluorescence signal change from red to purple. Detection mechanism proceeds via oxidation reaction of the probe by hypochlorite releasing the fluorescent 9-aminomethlyanthracene unit as verified by TOF-MS, 1H NMR and IR spectra. The experimental results demonstrate thatIMA has excellent sensitivity, low detection limit (0.29 μM), fast response time and high pH stability for hypochlorite.By employing IMA on a TLC test kit and in real samples, the hypochlorite level is successfully determined. Moreover, IMA allowed the fluorescence bioimaging of hypochlorite ions in yeast cells.