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A chalcone series ( 3a - f ) with electron push-pull effect was synthesized via a one-pot Claisen-Schmidt reaction with a simple purification step. The compounds exhibited strong emission, peaking around 512-567 nm with mega-stokes shift (∆λ = 93-139 nm) in polar solvents (DMSO, MeOH, and PBS) and showed good photo-stability. Therefore, 3a - f were applied in cellular imaging. After 3 h of incubation, green fluorescence was clearly brighter in cancer cells (HepG2) compared to normal cells (HEK-293), suggesting preferential accumulation in cancer cells. Moreover, all compounds exhibited higher cytotoxicity within 24 h toward cancer cells (IC 50 values ranging from 45 to 100 μM) than normal cells (IC 50 value &gt;100 μM). Furthermore, the antimicrobial properties of chalcones 3a - f were investigated. Interestingly, 3a - f exhibited antibacterial activities against Escherichia coli and Staphylococcus aureus , with minimum bactericidal concentrations (MBC) of 0.10-0.60 mg/mL (375-1000 µM), suggesting their potential antibacterial activity against both Gram-negative and Gram-positive bacteria. Thus, this series of chalcone-derived fluorescent dyes with facile synthesis shows great potential for the development of antibiotics and cancer cell staining agents.

Photophysical Study and Biological Applications of Synthetic Chalcone-Based Fluorescent Dyes