Synthesis, Structures And Properties Of4-Substituted Pyrene Derivatives

Organic photoelectronic materials have attracted extensive attention and become widely studied for its rapid development and tremendous potential application value. To build a series of different structural molecules and explore the structure-property relationship is the core of organic electronics.Since the1970s, metal-catalyzed coupling reaction has gradually become one of the most useful carbon growth methods in organic synthesis. Suzuki as one of typical coupling reaction, the key substrate is the aryl boronic acids (or borates). Therefore, by means of synthesizing aryl boronic acids (or borates), and work over its activity to derivatization will be the starting point of this thesis.The paper selects pyrene as parent, focusing on the varying characters of different site (namely1,3,6,8-position;2,7-and4,5,9,10-position). By the use of Ir-catalyzed derect C-H borylation, several pyrene borates substituted in different position have been synthesized. We researched their activities, photophysical properties and obtained single crystal structures some of them. The main results are as following:1. Two new4-position substituted pyrene borates derivatives were reported in this thesis, which overthrew the previous conclusion "C-H borylation generally not take place ortho to ring junctions.’ 2. Two new4-position toly substituted pyrene derivatives were synthesized by Suzuki coupling reaction. This gave a strong evidence that the4-position substituted pyrene borates is active to derivative.3. The differences of UV-vis and emission spectra between1-,2-, and4-position substituted pyrene were examined.2-substituted has little influence on the S2←S0excitation, but a strong influence on the S1←S0excitation. In contrast, the1-substituted derivatives display a strong influence on both the S1←S0and the S2←S0excitation. However,4-substituted shows the peculiar properties.4. A novel4-position sulfur bridged phenyl-pyrene compound BTP (benzothioxpyrene) was synthesized. It has good planarity, large conjugation and electron-rich nature, which make it potentially applied in OFET. The structure, optical and physical properties were discussed.