Synthesis of an efficient Pyrene based AIE active functional material for selective sensing of 2,4,6-trinitrophenol

Abstract

Abstract Aggregate/solid-state fluorescence switching organic material, 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (PAP) was synthesized via simple one-step synthetic process. It exhibited novel aggregation induced emission (AIE) phenomenon by controlling water ratio in solutions which provide sturdy cyan emissive fluorogenic aggregates with diverse well-defined morphologies, especially tuning the morphologies from 0-D to 1-D microcrystals that show obvious optical waveguide effect. Dynamic light scattering, time-resolved photoluminescence, optical fluorescence microscope and scanning electron microscope were exploited to gain insight into the AIE mechanism and discrimination of the different aggregated morphologies such as 0-D hollow spheres, 1-D hexagonal, hexagonal 1-D growth, rods and wires with distinct emissions tuning in solid state. Intriguingly, triple excitation induced triple emissions of green, yellow and red lights were emanated from microstructures in solid state for the first time which completely covered visible spectral region. By taking the advantage of its attractive AIE feature, the fluorescent hydrosol employed itself as a fluorescent chemosensor with superb selectivity and sensitivity toward explosive TNP through ground state complexation with a detection limit as low as 16 nM and very high Stern–Volmer quenching constant of 4.7 × 10 5 M −1 . An instant ‘naked eye’ response for trace detection of TNP in solid state, we prepared the fluorescent paper strips which make the protocol simple, fast, inexpensive and practical for on-site visualization.