Pyrene-contg. water-sol. probes for the fluorescent detection of nitroarom. compds. (NACs), such as explosive components (2,4-DNT and 2,4,6-TNT) and herbicides (2,4-dinitrocresol, 2,4-DNOC), in aq. media are reported. In the probes, the introduction of surface-active hydrophilic heads at the periphery of lipophilic (i.e., hydrophobic) pyrene tails resulted in the formation of highly fluorescent micelle-like aggregates/pre-assocs. in aq. solns. at concns. of ≤10-5M. The enhanced fluorescence quenching of the herein reported architectures is achieved in the presence of ultra-trace amts. of TNT or 2,4-DNT with values of Stern-Volmer quenching const. close to 1 × 105M and a detection limit as low as 182 ppb. The most hydrophilic probes demonstrated higher response to 2,4-DNT over TNT. Filter paper test strips impregnated with 1 × 10-5M solns. of the probes were able to detect TNT, 2,4-DNT, and other NACs at levels as low as 50 ppb in water.
