Synthesis And Properties Of Fluorescent Dyes Based On Helicenes

Organic fluorescent dyes have very good optical physical properties,such as:high fluorescence quantum yield,large Stokes shift,light stability,etc.,but due to?-?stacking and intermolecular interactions,fluorescence will undergo aggregation induced quenching?ACQ?.Spirene is a type of compound with ortho-condensation,helical chirality and non-planar aromatic structure.The large conjugated system,spiral non-planar nature makes it a very good fluorescent compound skeleton.By reading a large number of related literature and exploring the mechanism of fluorescence generation,a series of spiroallene-based organic fluorescent dye compounds were designed and synthesized 2-10,2-11,2-12,2-13,2-14,2-16,.2-17,2-19,such compounds not only have good photophysical properties in solution,but also have the same state in the solid state.The NMR spectra?hydrogen spectrum,carbon spectrum?and high resolution mass spectrometry were used to characterize the compounds.The photophysical properties of the compounds were investigated by UV absorption spectra and fluorescence emission spectra.The compounds 2-10 were tested in pure dichloromethane and they were not specific.Compounds 2-11,2-13,and 2-16 can be well regulated with volatile acids and bases in both solution and solid state.Reversibility and fatigue resistance;compounds2-12 have an aggregation-induced red-shift property;compounds 2-14,2-17self-assemble with electron-rich molecules and have poor performance;compounds 2-19can recognize rare earth metal ions Eu³⁺.