The Synthesis And Properties Of Perylene Diimides Fluorescence Probes Modified By Morpholine

Perylene diimides exhibit many favorable properties, such as remarkable photochemical stability, excellent photoelectric characteristic, high fluorescence quantum yield and easy modification, which made the compound of perylene diimides a hot research topic. In this thesis, we designed and synthesized several compounds of perylene bisimide with enhanced fluorescence property by the introduction of hydrophilic PEO chain and morpholine moiety into perylene bisimide. The main contents of this thesis are as following.1. Fluorescent probes, AMPD and SMPD, were synthesized by introducing morpholine moiety into the bay region of perylene diimides. The florescence properties of the two probes were studied in different p H buffer solution, and then the p Ka values of AMPD and SMPD were calculated to be 5.62 and 5.36, respectively. They show the response of the fluorescence enhancement to the change of the p H. Living cell fluorescence experiments indicate that:AMPD and SMPD probes can be internalized by live cells; the strong hydrophobic nature results in their increased non-specificity to intracellular substance, which makes them don't have the targeting action to lysosomal acidic organelle.2. AMPG and SMPG with good water-solubility were obtained by the introduction of the hydrophilic PEO chain into the imides. The florescence properties of the two probes were studied in different p H buffer solution, and then the p Ka values of AMPG and SMPG were calculated to be 5.31 and 5.17, respectively. As the solution changes from basic to acid, the fluorescence intensity of AMPG shows 25-fold increase and SMPG shows 158-fold.Meanwhile, the probes show good reversibility between p H 4.0 and p H 8.0.3. The cytotoxicity experiment shows that the cell survival rates of the two probes are more than 85% and 90%, respectively, indicating good biocompatibility. Cell imaging experiments show that, AMPG and SMPG can penetrate cell membrane and stain cell cytoplasm region. The colocalization experiments show that: AMPG and SMPG can be used in living cell fluorescence imaging, and located in lysosomes efficiently with Pearson's coefficient of 0.9080 and 0.9230, respectively. Light stability erperiments show that the fluorescent probes have good stability in cells.