Design And Synthesis Of Pyrene Derivatives And Their Application For Metal Ion Recognition And Molecular Logic Gates

Since the pioneering work of Laurent, who in 1837 discovered pyrene in the residue of the destructive distillation of coal tar, this polycyclic aromatic hydrocarbon has been the subject of tremendous investigation. Its unique properties have inspired researchers from many scientific areas. Especially,since the palladium-catalyzed cross-coupling reaction was found, such as the Heck Coupling Reaction-. the Sonogashira Coupling Reactiong-. the Suzuki Coupling Reaction, the chemical modification on the pyrene has have a further development. On the other hand, given their sensitivity the fluorescent probes have several advantages over other methods, real-time monitoring with fast response, high selectivity, and simple operation. So they are widely used for the detection of heavy metal ions in environmental and biological systems. In this thesis, the derivative of pyrene containing Scciff base structure was successfully synthesized by bromine substitution reaction, Sonogashira Coupling reaction and condensation reaction. The molecule containing pyrene unit has a strong yellow-green flourescence itself; the periphery of molecule contains nitrogen atom which can coordinate with metal ions. Verified by fluorescence measurements, the fluorescent probes can selectively identify Ni2+ and Pb2+. The specific contents are follows:1. The pyrene derivatives with functional groups identifying metal ions have been successfully synthesized by bromine substitution reaction, Sonogashira Coupling reaction and condensation reaction. Through the common characterization methods in laboratory, such as nuclear magnetic resonance(NMR), infrared spectrometer(IR), ultraviolet and visible spectrophotometer(UV) and high-resolution mass spectrometry(HRMS), the product and intermediates are proved that they are consistent with the materials designed.2. The spectral properties of the final product can be analyzed by uv-vis spectrophotometer and fluorescence spectrophotometer. By the dropping method, metal ions in aqueous solution were added to DMF solution of the fluorescent molecular probes. Then we watched the fluorescent changes and found that the fluorescent molecular probe was able to identify the metal ions.3. we measure the response of the fluorescent probe system while inputting signals such as Ni2+、Pb2+、EDA, and analyze the application of fluorescent probe in the molecular logic gates.