Fluorescent Chemosensors with Varying Degrees of Intramolecular Charge Transfer for Detection of a Nerve Agent Mimic in Solutions and in Vapor

Nerve agents are highly toxic organophosphorus compounds, and their possible use in terrorist attacks has led to increasing interest in the development of reliable and accurate methods to detect these lethal chemicals. In this paper, we have prepared six 6-aminoquinolines with various N-substituents as chemosensors for a nerve-agent mimic diethylchlorophosphate (DCP). The chemosensors with the nucleophilic pyridine-N atom as the active site detect DCP via a catalytic hydrolysis approach to form the protonated sensor. The nucleophilicity of the pyridine-N atom depends on the donating ability of the 6-amine group, which affects the intramolecular charge-transfer (ICT) character of sensors and the protonated sensors, leading to different fluorescence-response modes. The effects of the ICT character on the sensing property have been clarified. Among these charge transfer sensors, the sensor 3 displays ratiometric fluorescence response to DCP and a low limit of detection (8 nM). Furthermore, a facile testing strip with 3 has been fabricated with poly(ethylene oxide) for real-time selective monitoring of DCP vapor.