Quinoline-2-thione-based fluorescent probes for selective and sensitive detections of mustard gas and its analogues

Abstract

Sulfur mustard (SM, also called as mustard gas (HD)) is a persistent and highly toxic gas used as chemical weapon in wars and military conflicts. Moreover, owing to its simple structure and easy synthesis, it is the most likely chemical agent used by terrorists. For this reason, it is vital important to develop a facile, rapid and reliable detection system for SM. In this paper, we have developed four quinoline-2-thiones as fluorescent probes, 2a-2d, for the detection of SM and its analogues, half sulfur mustard (CEES) and a nitrogen mustard NH1. In the presence of KOH, these quinoline-2-thiones deprotonated to quinoline-2-thiophenol anions, which react with SM and its analogues rapidly to form quinoline-2-thiethers with highly efficient fluorescence, giving turn-on fluorescence response. The sensing products with CEES were isolated and fully characterized, thereby, the sensing mechanism was firmly established. The fluorescent probes with 4-trifluoromethyl group, 2b and 2d, exhibit rapid response to SM, CEES and NH1 (within 1 min at 60 °C for CEES and NH1), high sensitivity (limit of detection, 50 nM for SM and 20 nM for NH1) and high selectivity. Furthermore, polymer film test strips were fabricated with probe-embedded poly(ethylene oxide) for the detection of CEES vapor. These test strips displayed a rapid response (<4 min) to gaseous CEES with high sensitivity (0.2 ppm) and high selectivity. These results show that fluorescent probes 2b and 2d have a good application prospect in the field detection of mustard gas.