An excited-state intramolecular proton transfer (ESIPT)-based aggregation-induced emission active probe and its Cu(II) complex for fluorescence detection of cysteine

Abstract

In this work, an effective and simple aggregation-induced emission (AIE) active fluorescent probe based on ESIPT luminescence principle, 2-hydroxy-1-naphthal-4-aminoantipyrine (1), was synthesized via a simple chemical reaction. It displayed strong fluorescence enhancement in water. The AIE mechanism of 1 was explored by electron microscopy and computational analysis. We demonstrate the combination effect of intramolecular hydrogen bonds and π-π stacking to endow 1 with such a property. Importantly, the ensemble of 1 with copper ions (Cu-1) as a fluorescent probe enables highly selective and sensitive turn-on fluorescence detection of cysteine (Cys) over other interfering substances. Under optimal detection conditions, this probe has a good linear relationship in the concentration range of Cys between 0 and 8 μM, and the detection limit of Cys was estimated as 84 nM. Furthermore, this assay exhibits good reversibility of 1 to Cu2+ and Cys. Due to its good biocompatibility evaluated by CCK-assay, the probe Cu-1 was finally applied in imaging of Cys within Min6 cells successfully.