The development of aggregation-induced emission enhancement (AIEE) active nanoprobes without any synthetic complication for solution-state and organic thin-film transistor (OTFT)-based sensory applications is still a challenging task. In this study, the novel pyrene-incorporated Schiff base (5-phenyl-4-((pyren-1-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol; PT2) with an AIEE property was synthesized via a one-pot reaction and was reported for detecting Zn 2+ and tyrosine in the solution state and OTFT. In the AIEE studies of PT2 (in CH 3 CN) at various water fractions (f w : 0− 97.5%), the existence of J-aggregation, crystalline changes, and nanofibers formation was confirmed by ultraviolet absorption/photoluminescence (UV/PL) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), and dynamiclight scattering (DLS) techniques. Similarly, PT2-based Zn 2+ detection and sensory reversibility with tyrosine were demonstrated by UV/PL studies with evidence related to crystalline/nanolevel changes in PXRD, SEM, TEM, AFM, and DLS data. Distinct decay profiles associated with the AIEE and sensory responses of PT2 were observed in time-resolved photoluminescence spectra. From the standard deviation and linear fittings of PL titrations, detection limits (LODs) of the Zn 2+ with PT2 and the tyrosine with PT2-Zn 2+ were estimated as 0.79 and 45 nM, respectively. High-resolution mass and 1 H NMR results confirmed 2:1 and 1:1 stoichiometry and binding sites of PT2-Zn 2+ -PT2* and tyrosine-Zn 2+ complexes. Moreover, the values of association constants determined by linear fittings were 4.205 × 10 −7 and 1.73 × 10 −8 M −2 , correspondingly. Optimization via the density functional theory disclosed the binding sites and suppression of twisted intramolecular charge transfer/photoinduced electron transfer (TICT/ PET) as well as the involvement of restricted intramolecular rotation in the AIEE and PET "ON-OFF-ON" mechanisms in the Zn 2+ and tyrosine sensors. Results from the B16−F10 cellular and zebrafish imaging of AIEE, Zn 2+ , and tyrosine sensors further attested the applicability of PT2 in biological samples. Finally, the PT2 and pentacene-incorporated OTFT devices were fabricated. The devices displayed more than 90% change in drain-source current when reacted with Zn 2+ with an LOD of 5.46 μM but showed no response to tyrosine, thereby confirming the reversibility. Moreover, the OTFT devices also demonstrated Zn 2+ ion detection in tap water and lake water samples.