A novel water-soluble fluorescent polymer based on perylene bisimides dyes: one-pot preparation and its bio-imaging

Abstract

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.

Synthesis and Self‐Assembly of Bay‐Substituted Perylene Diimide Gemini‐Type Surfactants as Off‐On Fluorescent Probes for Lipid Bilayers

“…For bioimaging, fluorescent quenching of PDIs has been used to sense hydrophobicity changes such as in artificial and cellular bilayers 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. However, PDIs as highly sensitive fluorescent probes with a low background signal are still rare.…”

“…[7][8][9] For bioimaging, fluorescent quenching of PDIs has been used to senseh ydrophobicity changess uch as in artificial and cellular bilayers. [10][11][12][13][14][15][16][17][18][19][20] However, PDIs as highly sensitive fluorescent probes with al ow background signal are still rare. Such off-on fluorescentp robesw ould be appealing for cellular imaging.…”

Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells

“…However, the difficulty comes from the strong intermolecular π–π interactions of PBIs’ large aromatic core, which causes water insolubility [4,5]. Several studies have focused on introducing ionic groups or attaching water-soluble polymers to its bay or imide positions [6,7]. For example, Müllen et al introduced ionic aromatic systems, such as phenoxy substituents with sulfuric acid residues, pyridinium salts, or quaternary ammonium salts, at its bay positions to suppress aggregation in water [8].…”