Phenothiazines are highly active and attracting significant attention in various fields including biology and medicine, etc. Herein, several styryl phenothiazine derivatives including VPPA, VPBM, 3PVP and 4PVP were successfully synthesized, and their relationship of functional groups and photophysical properties was investigated in detail. Among them, VPPA demonstrated twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) properties, while 4PVP with phenothiazine-pyridine structure demonstrated aggregation-caused quenching (ACQ) effect and obvious pH sensitivity for targeting potential in various pH environments. In order to explore AIE and ACQ effects, a series of fluorescence performances, molecular electrostatic potential (ESP), stacking models, and quantization calculations were conducted. Subsequently, 3PVP, 4PVP and VPPA were copolymerized by RAFT polymerization with PEGMA for their potential in intracellular imaging and drugs delivery, and the obtained copolymers self-assembled in aqueous solution into fluorescent nanoparticles with about 150 nm with low toxicity and good biocompatibility. Drugs delivery systems of VA-PTX FONs and 4VP-PTX FONs with the anti-tumors drug paclitaxel (PTX) could successfully release PTX with high toxicity to the A549 cells, which respectively decreased the cells viability to 31.84 % and 26.90 %, showing high cells inhibition ratio. The as-prepared drug-delivery nanoparticles have perspective potential in visualizing, bioimaging, medical diagnostics, and drugs track.
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