Active Hydrogen Free, Z-Isomer Selective Isatin Derived "Turn on" Fluorescent Dual Anions Sensor.

Abstract

An efficient and anions fluorescence "on-off" sensor of 1-(prop-2-yn-1-yl)-3-(quinolin-3-ylimino)indolin-2-one (PQI) has been developed for the selective sensing of dual anions of F- and NO3- ions in aqueous medium. Active hydrogen and Lewis acidic binding sites free, Z- isomer of isatin based π-conjugated quinoline exhibited excellent sensing activity against F- and NO3- ions in UV light. The fluorescence turns on the process accomplished via the PET "on-off" mechanism. The interaction between probe molecule and anions is thought to be a non-covalent interaction of the low electron density covalently bonded N-methylene moiety of propargyl isatin (-N-CH2-) of probe molecule with F- ion and the terminal acidic proton of propargyl group of isatin (-C≡C-H) with NO3- ions. The modes of anions binding with PQI and plausible mechanisms are proposed by 1H and 13C NMR titrations. The selectivity of anions sensing may be offered by the bucked structure of the Z-isomer. The calculated association constant values for PQI and F- and NO3- are ions 2.5 × 104M-1 and 2.2 × 103M-1, respectively, indicating strong binding interaction between the PQI and anions. The association nature of anions and probes was analyzed by a Jobs plot and the finding indicates both F- and NO3- ions are in 1:1 complexation with PQI. The limit of detection (LOD) of the probe with F- and NO3- ions is calculated and is to be 6.91 × 10-7M and 9.93 × 10-7M, respectively. The proposed PQI fluorophore possesses a low limit of detection (LOD) for both F- and NO3- ions which is within the WHO prescribed detection limit.