Easily available aggregation-induced enhanced emission fluorescent material for detecting 1, 3-diaminopropane in gas-liquid-solid three-phase and bioimaging application

Highlights: • L can effectively detect 1,3-diaminopropane (Dap) and offers a remarkable AIEE. • L can be used to identify Dap by the naked eye in gas, liquid, and solid. • L-Dap has potential for fingerprint recognition based on AIEE. • L showed low cytotoxicity and successfully determined Dap in vitro and in vivo with a "turn-on" fluorescence. Polyamine plays the important role in human body. Here, the convenient synthesis of AIE material 2-(pyren-1-ylmethylene) malononitrile (L) was capable of fluorescent recognition for 1, 3-diaminopropane in gas-liquid-solid three-phase with good selectivity and high sensitivity. And it's interesting that other amines did not interfere with the recognition between L and 1,3-diaminopropane. The proposed sensing mechanism was supported by Job's plots, ¹H NMR titration, FT-IR, electron-spray ionization, and density functional theory calculation analysis. The limits of detection were estimated as 1.34 × 10⁻⁸ M. The self-made test strips and silica gel plates realized the easy detection of 1, 3-diaminopropane. L-1, 3-diaminopropane possessed the potential for fingerprint recognition based on AIEE in the silica gel plates developed within this study. Notably, bioimaging in seeds, plant tissues, Caenorhabditis elegans, and mice revealed that L could be suitable as an effective sensor for detecting 1, 3-diaminopropane in living systems with the strong "turn-on" fluorescence. Importantly, L showed good biocompatibility and could effectively recognize 1, 3-diaminopropane and reveal its location with colored AIEE fluorescence in HeLa cells.