Naphthalimide and Carbazole Based Mechanochromic Molecular Dyads and Triads for Selective Lysosome Imaging

In this study, we report the design and development of a stable fluorescent probe that is selectively localized in the cytosol of Hela cells. We designed two probes, 1 and 2, with D-π-A (carbazole (Cbz)-vinyl-naphthalimide (NPI)) and A-π-D-π-A (NPI-vinyl-Cbz-vinyl-NPI) architecture, respectively. Probes 1 and 2 exhibit broad photoluminescence (PL) spectra ranging from green (550 nm) to far-red (800 nm) in solutions and aggregated states. In the solid-state, the PL of these probes shows a bathochromic shift, which can be attributed to intermolecular interactions. In a water-rich medium, Probe 1, with a single NPI moiety, shows aggregation-caused quenching (ACQ) but retains a moderate quantum yield of 13.7 % (Φ_soln=61.4 %). On the other hand, probe 2, with two NPI units, showed aggregation-induced enhanced emission AIEE, where the PLQY is increased nearly 4 times (Φ_soln=3.5 %, Φ_agg=12.8 %). In-vitro cell studies revealed that these probes are non-toxic and effectively stain cells in green and red channels. Notably, Probe 1 demonstrated excellent cellular uptake and selectivity for lysosome, with a Pearson overlap coefficient of 0.91.