Strong Blue Emissive Supramolecular Self-Assembly System Based on Naphthalimide Derivatives and Its Ability of Detection and Removal of 2,4,6-Trinitrophenol.

Two simple and novel gelators (G-P with pyridine and G-B with benzene) with different C-4 substitution groups on naphthalimide derivatives have been designed and characterized. Two gelators could form organogels in some solvents or mixed solvents. The self-assembly processes of G-P in a mixed solvent of acetonitrile/H2O (1/1, v/v) and G-B in acetonitrile were studied by means of electron microscopy and spectroscopy. The organogel of G-P in the mixed solvent of acetonitrile/H2O (1/1, v/v) formed an intertwined fiber network, and its emission spectrum had an obvious blue shift compared with that of solution. By contrast, the organogel of G-B in acetonitrile formed a straight fiber, and its emission had an obvious red shift compared with that of solution. G-P and G-B were employed in detecting nitroaromatic compounds because of their electron-rich property. G-P is more sensitive and selective toward 2,4,6-trinitrophenol (TNP) compared with G-B. The sensing mechanisms were investigated by 1H NMR spectroscopic experiments and theoretical calculations. From these experimental results, it is proposed that electron transfer occurs from the electron-rich G-P molecule to the electron-deficient TNP because of the possibility of complex formation between G-P and TNP. The G-P molecule could detect TNP in water, organic solvent media, as well as using test strips. It is worth mentioning that the organogel G-P can not only detect TNP but also remove TNP from the solution into the organogel system.