Naphthalimide-Based Fluorophore for Soft Anionic Interface Monitoring.

Abstract

A naphthalimide-based low-molecular-mass fluorophore (NA) was designed and synthesized by introducing an azetidine unit onto the aromatic ring of the compound as an electron-donating structure, and a hydrophilic (2-(2-aminoethyl-amino)ethanol) moiety into the "N-imide site" of the core structure. UV-vis absorption and fluorescence measurements revealed that the fluorophore is soluble in water and shows a fluorescent quantum yield of ∼20% and lifetime of ∼3.7 ns in the solvent within a wide pH range. Moreover, the fluorescence emission and anisotropy of the fluorophore as produced are both dependent upon the viscosity and polarity of the medium. Further studies demonstrated that NA can be used as a selective probe to monitor the aggregation of anionic surfactants owing to its accumulation onto the anionic surfaces of the aggregates as formed. Inspired by the discovery, NA was successfully applied for detection of cell membranes and E. coli via monitoring of their negatively charged surfaces, which is important for fast checking of biological contamination of water. Importantly, all the tests could be performed in a visualized manner. We believe that the new, low-molecular-mass fluorophore as created may find applications in chemical and biochemical sensing and imaging.