Dansyl-based fluorescent film sensor for nitroaromatics in aqueous solution

We demonstrate the preparation, characterization and performance evaluation of a fluorescent film sensor for the specific detection of nitroaromatics in aqueous solution. The film sensor was fabricated by covalent immobilization of a fluorophore, dansyl, on a glass slide surface via reaction with diaminopropane and then with an epoxide-terminated self-assembled monolayer. Nitroaromatics like nitrobenzene, 4-nitrotoluene, 3,5-dinitrotoluene, and 2,4,6-trinitrotoluene, etc were found to strongly quench the fluorescence emission of the film while some other commonly-used quenchers like nitromethane, KI, acrylamide, etc showed no or slight quenching effect on the emission. The quenching mechanism was examined through fluorescence lifetime measurements and it was proved that the quenching is static in nature and may be caused by electron transfer from the fluorophore to the nitroaromatics. The presence of other aromatics like benzene, toluene, etc had little effect upon the sensing performance of the film to nitroaromatics. Solvent effect studies revealed that the conformations adopted by the spacer connecting the fluorophore and the substrate played a crucial role in the performance of the film sensor. Furthermore, the response of the film to nitroaromatics is fast and reversible.