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Perylene bisimides dye-based water-soluble fluorescent polymer P3, N,N'-bis(3-amyl)-1-bromo-7-{4'-[3''-(S-poly(N-acryloyl ethylene diamine hydrochloride)-2'''-methyl propionic acid)propionyloxy hexyloxy]phenyl} perylene-3,4:9,10-tetracarboxylic bisimides, was synthesized with polyelectrolyte modification via one-pot reaction (the reduction reaction of trithioester and click reaction between the thiol group and carbon-carbon double bond were simultaneously conducted in one pot with high conversion). One-pot method can overcome the limitation that usual click reaction between thiol and other groups has low conversion because thiol group is subject to rapid oxidation during purification and storage. Chemical, structural, and optical properties of P3 and intermediate products were fully characterized by nuclear magnetic resonance spectroscopy, Fourier transform infrared, gel permeation chromatograph, UV-vis spectra, and fluorescence spectra, respectively. The results revealed that P3 displayed excellent water solubility and not only exhibited red strong fluorescence emission band in water but also had the similar photoluminescent spectra to those of intermediate products (M4 and P2) in chloroform. Allowing for the potential application in biological detection field, cell viability and live cell imaging with the presence of P3 were further investigated with Hela cells. The results showed that P3 had low cytotoxicity with strong intracellular fluorescence entry. Meanwhile, with the augment of concentration of P3 (0-0.500 mg mL(-1)), the cell uptake and accumulation of P3 increased and thereby result in enhancement of the intracellular fluorescence. These experiment results suggested that P3 had enormous potential as a fluorescence probe to be an important component in biological detection field.

Perylene bisimides dye-based water-soluble fluorescent polymerP3,N,N’-bis(3-amyl)-1-bromo-7-{4’-[3’’-(S-poly(N-acryloyl ethylene diamine hydrochloride)-2’’’-methyl propionic acid)propionyloxy hexyloxy]phenyl} perylene-3,4:9,10-tetracarboxylic bisimides, was synthesized with polyelectrolyte modification via one-pot reaction (the reduction reaction of trithioester and click reaction between the thiol group and carbon–carbon double bond were simultaneously conducted in one pot with high conversion). One-pot method can overcome the limitation that usual click reaction between thiol and other groups has low conversion because thiol group is subject to rapid oxidation during purification and storage. Chemical, structural, and optical properties ofP3and intermediate products were fully characterized by nuclear magnetic resonance spectroscopy, Fourier transform infrared, gel permeation chromatograph, UV–vis spectra, and fluorescence spectra, respectively. The results revealed thatP3displayed excellent water solubility and not only exhibited red strong fluorescence emission band in water but also had the similar photoluminescent spectra to those of intermediate products (M4andP2) in chloroform. Allowing for the potential application in biological detection field, cell viability and live cell imaging with the presence ofP3were further investigated with Hela cells. The results showed thatP3had low cytotoxicity with strong intracellular fluorescence entry. Meanwhile, with the augment of concentration ofP3(0–0.500 mg mL−1), the cell uptake and accumulation ofP3increased and thereby result in enhancement of the intracellular fluorescence. These experiment results suggested thatP3had enormous potential as a fluorescence probe to be an important component in biological detection field. [ABSTRACT FROM AUTHOR]

We report the synthesis and properties of perylene diimides with fluorinated substituents on the bay ( BFPDI s). These BFPDI s exhibit good water solubility, high extinction coefficients, and high fluorescence quantum yields. Furthermore, these BFPDI s are used as probes in cellular imaging. [ABSTRACT FROM AUTHOR]

We prepared the peri-linked perylene dyes with π bridges ( PLPDB ) by palladium-mediated coupling reaction. These PLPDB dyes exhibited increased Stokes shifts (55–66 nm) and high fluorescence quantum yields (85–96%) due to cyclic molecular dynamics process. The PEGylated PLPDB dyes were synthesized by attaching PEG pendants to fluorene bridges, and these PEGylated dyes displayed good water solubility and extremely large Stokes shifts (112 nm) in water. The cells incubated with the PEGylated PLPDB dyes showed over 85% cell viability, indicating good cytocompatibility. Live cells image indicates that the PEGylated PLPDB dyes can be efficiently internalized and accumulated by live cells. [ABSTRACT FROM AUTHOR]