Anthracene-based fluorescent probe: Synthesis, characterization, aggregation-induced emission, mechanochromism, and sensing of nitroaromatics in aqueous media

Abstract

The sensitive and selective detection of nitroexplosive molecules thorough a simple methodology has received a significant field of research affecting global security and public safety. In the present study, the synthesis of anthracene-based chalcone (S1) was conducted using a simple condensation method. S1 was found to exhibit unique properties, such as aggregation-induced emission in solution and mechanochromic behavior in solid state. A fluorescent aggregate was applied to sense electron-deficient picric acid (PA) and 2,4-dinitrophenol (2,4-DNP) in an aqueous solution. Notably, the developed test strip-based sensor (S1) could be used to effectively detect PA and 2,4-DNP, which were visualized by the naked eye. Photophysical analysis revealed the occurrence of an electron transfer from electron-rich S1 to the electron-deficient nitro compounds, which was confirmed using density functional theory and ¹H-nuclear magnetic resonance studies. In addition, the observed results confirmed the simple synthesis of S1 as a promising material for the development of test strip-based sensor devices for the detection of toxic and explosive aromatic nitro molecules.

Keywords: 2,4-Dinitrophenol; Aggregation-induced emission; Anthracene-based chalcone; Picric acid; Sensor.