Synthesis, Photoelectric Properties And Bioactivities Of Nitrogen-containing Heterocyclic-Tr(?)ger’’s Base

The huge rigidity, V-shaped configuration and C2 axial chirality of Tr?ger’s base(TB) make itself be widely used in molecules recognition, chiral ligand, chiral solvent, molecules biomimetic receptor, cage-like body and DNA probes, etc. Recently, TB and its derivatives have become again the research hotspot in organic chemistry, medicinal chemistry, polymer chemistry etc. To further enrich the types of such compounds and to broaden its range of applications, this dissertation designed and synthesized three series of new TB derivatives and studied their luminescence and anti-cancer activity.This dissertation includes the following five chapters:In chapter 1, the research progress of TBs at home and abroad was summarized and the synthesis, properties and applications of TB derivatives were reviewed. Also, the selected topic basis, significance, design thought and innovation of this dissertation were put forward.In chapter 2, by Pd(0)-catalyzed Suzuki coupling and CuI-catalyzed Ullamann coupling, nine thiophene substituted luminous organic small molecule 3a-3g and 3h-3i based on TB framework were designed and synthesized. The structure of all products were confirmed by 1H NMR, 13 C NMR and HRMS. The Uv-vis spectra, fluorescence spectroscopy, electrochemical performance, thermal stability and theoretical calculation of all products were also tested and the results showed that this type of compound have excellent optical properties and thermal stability.In chapter 3, by CuI-catalyzed Ullamann coupling, indole, benzimidazole, benzothiazole or benzopyrazole fragment was introduced in TB framework to obtain six new luminous organic small molecule 4a-4f. The structure of all products were confirmed by 1H NMR, 13 C NMR and HRMS. The Uv-vis spectra, fluorescence spectroscopy, electrochemical performance, thermal stability and theoretical calculation of all products were also tested and the results showed that this type of compound have excellent optical properties and thermal stability.In chapter 4, by Pd(0)-catalyzed Suzuki coupling and CuI-catalyzed Ullamann coupling, terpyridyl(5a) or luminol(5b) substituted TB were designed and synthesized. Their metal ion recognition capability was tested subsequently. The results indicated that compound 5a has highly selectivity to Ce3 + and Cu2 + and compound 5b has highly selectivity to Ba2 + and Cu2 +. The results open up their application as fluorescence probe in ion detection in the future.In chapter 5, anti-tumor activity of TB derivatives was detected. The results showed that compound 3g, 4f and 5b have strong inhibition against four kinds of tumor cells, Compound 3h, 4a, 4b, 5a of human liver cancer cells(MHCC-97-h) inhibition is much higher than the other three kinds of tumor cell inhibitory effect on human liver cancer cells have a highly selective inhibition. The results open up their application as new anti-cancer drug in the future.