Synthesis And Application Of Responsive Fluorescent Nanomaterials Based On Perylene Imide

The application of stimuli-responsive materials in the fields of intelligent sensing,catalysis,anti-counterfeiting science,information encryption,nanotechnology and biology have become more and more widespread and attracted the attention of many researchers.To this end,this thesis is guided by functions such as temperature sensing and optical switch,using perylene diimide derivatives with unique photoelectric properties as the main body,and modifying the amphiphilic groups at both ends of perylene diimide to obtain perylene diimide supramolecules.The self-assembly behavior of the substance in DMF / H2 O system and the effect of temperature on the spectral properties of the fluorescent nanoparticles formed by self-assembly were studied.In addition,light-switching fluorescent polymer nanoparticles was prepared by one-step fine emulsion polymerization using perylene diimide derivative and diarylethylene compound,and the responsiveness and fatigue resistance of the optically switched polymer nanoparticles were explored.And apply it in the field of optical rewritable patterns.The main contents and results of this paper are as follows:1.UPy-PDI-UPy were synthesized by a click chemistry reaction using The amphiphilic 2-ureido-4 [1H]-pyrimidinone mercapto derivative UPy-SH and the perylene diimide compound DAC-PDI.and using the same method to synthesize two similar perylene diimide compounds UPy-TPDI-UPy,TEG-PDI-TEG,combined with nuclear magnetic and mass spectrometry and other characterization methods to confirm their structure.Further spectroscopic studies show that UPy-PDI-UPy solid-state fluorescence quantum yield is higher than that of two other perylene diimides with similar structure.2.Using the amphiphilic characteristics of the UPy-PDI-UPy structure,self-assembly in a mixed solution of N,N-dimethylformamide(DMF)and water in different ratios forms a series of supermolecular polymer fluorescent nanoparticles of different sizes.The investigation found that the supramolecular polymer fluorescent nanoparticles are highly sensitive to temperature.The temperature-responsive perylene diimide supramolecular polymer fluorescent nanoparticles and polyethylene glycols of different molecular weights were co-dissolved in DMF / H2 O mixed solvent(v / v = 50/50)at 45 ℃,Cooling to room temperature to obtain a series of temperature-sensitive gel systems.The results show that the fluorescence emission wavelength of the gel changes with temperature,and the solid fluorescence is light red at low temperature.When the gel turns into a sol,its fluorescence gradually changes to yellow-green.Such temperature-responsive supramolecular fluorescent nanoparticles are expected to be used as a temperature-responsive smart material in the field of controlled drug release.3.Based on the principle of fluorescence energy resonance transfer(FRET),the yellow-green fluorescent perylene diimide compound AC-PDI is used as the energy transfer donor,and the energy-matching optical switch molecule diarylethylene compound(DTE-DA)is used as the energy transfer,For the receptor.a light-switching fluorescent polymer nanoparticle was prepared by one-step fine emulsion polymerization,and a stable fluorescent polymer nanoparticle was prepared by AC-PDI.Then,the optical switch fluorescent polymer nanoparticles are made into a fluorescent rewritable thin film material.The fluorescent polymer nanoparticles are expected to be used in the fields of anti-counterfeiting and information storage.