Study On The Region-effect Of Regulating The Fluorescence Properties Of Pyrene Derivatives

The research content of this paper is in the field of organic photoelectric functional materials.Pyrene is a member of the typical fused aromatic hydrocarbon family because it has a rigid molecular plane,large π conjugates within the molecule,and interactions between molecules,often used to synthesize fluorescent materials and organic semiconductor materials.Pyrene has a wealth of derivative space.There are three kinds of sites with ten chemical reactivity and unique charge transport properties around the ruthenium molecule.What is the relationship between the nature of the indole derivative and the introduction site of the functional group on the pyrene?How to use the same group at different sites to regulate and influence the fluorescent properties of the pyrene derivative?It may be limited to the difficulty of synthesis,and no systematic and in-depth study of this issue has been reported in the literature.Therefore,we selected the regio-effect of pyrene as the theme,and explored the regio-effect of pyrene by designing,synthesizing,characterizing and testing the isomers of different sites of different groups,finding the relationship between structure and properties.We are looking forward to controlling the photoelectric performance of pyrene and providing a powerful reference for the development of various derivatives of pyrene.In the paper,we synthesized and characterized four series of 15 kinds of pyrene derivatives,and cultured single crystals of 8 compounds,7 of which were crystals obtained for the first time.Each series has a set of isomers.On this basis,we systematically studied the regio-effect of pyrene derivatives,especially the differences in substituent sites for photophysical properties and bioprobe targeting.The main results are as follows:1、.The isomers of PA were synthesized by using different sites of hydrazine.Its synthetic route confirms the chemical activity of pyrene.A single crystal diffraction structure of PA-2 and PA-4 was obtained.Low temperature phosphorescence of PA-2 was discovered.2、An anthracene derivative PB in which diamyl boron is an electron acceptor is synthesized.A single crystal diffraction structure of PB-4 was obtained.PB has a high quantum yield and its size order is PB-1>PB-2>PB-4.Spectroscopic experiments show that PB-1 is similar to PB-4,but the absorption of PB-4 is longer in blue emission and thus the Stoke displacement is larger.3、A series of indole cation fluorescent probes(Py)were synthesized.Py-4 and Py-1 have similar fluorescence quantum yields.The absorption spectrum of Py-4 is blue-shifted and its emission spectrum is red-shifted,so the Stokes shift is much larger than Py-1.Preliminary cell staining and fluorescence imaging experiments showed that t-Bu-Py-4 can be used as a mitochondrial probe with good selectivity and low cytotoxicity.4、A series of pyridinium cationic fluorescent probes(PP)were synthesized.Its fluorescence quantum yield is much higher than Pys.The fluorescence intensity of PP-1 and PP-4 is very high,and the emission peak of PP-4 has a significant red shift than PP-1.The order of positional effects of electron delocalization is:1-site>4-site》2-site.