A Versatile Naphthalimide-Sulfonamide-Coated Tetraphenylethene: Aggregation-Induced Emission Behavior, Mechanochromism, and Tracking Glutathione in Living Cells.

A tetraphenylethene (TPE) derivative substituted with a sulfonyl-based naphthalimide unit (TPE-Np) was designed and synthesized. Its optical properties in solution and in the solid state were investigated. Photophysical properties indicated that the target molecule, TPE-Np, possessed aggregation-induced emission (AIE) behavior, although the linkage between TPE and the naphthalimide unit was nonconjugated. Additionally, it exhibited an unexpected, highly reversible mechanochromism in the solid state, which was attributed to the change in manner of aggregation between crystalline and amorphous states. On the other hand, a solution of TPE-Np in a mixture of dimethyl sulfoxide/phosphate-buffered saline was capable of efficiently distinguishing glutathione (GSH) from cysteine and homocysteine in the presence of cetyltrimethylammonium bromide. Furthermore, the strategy of using poly(ethylene glycol)-polyethylenimine (PEG-PEI) nanogel as a carrier to cross-link TPE-Np to obtain a water-soluble PEG-PEI/TPE-Np nanoprobe greatly improved the biocompatibility, and this nanoprobe could be successfully applied in the visualization of GSH levels in living cells.