Synthesis And Characterization Of C-HBC Derivatives And Their Oligomers

The organic photolelectric materials are widely used in organic light emitting diode,organic transistor,organic solar cell,an organic memory and so on,due to easy processing,fast optical response and high storage density.There are some commonality and difference in these applications.The commonality is that semiconductor optoelectronic properties of these materials are used to improve performance response.The difference is that the different of the performance material requires different chemical structure to achieve.So we can see that there is a close relationship between performance and molecular structure.To study these relationship can help us to design and optimize new materials,explore novel devices.Polycyclic aromatic hydrocarbons as star materials in organic optoelectronic materials are mainly due to their excellent performance in optoelectronic devices.According to the form of fused aromatic hydrocarbons,they can be divided into two types: flat and non-planar.Compared with the planar fused aromatic hydrocarbons,the contorted structure has important ramifications on the inherent physical behavior of these materials.The intermolecular contacts in crystals and polycrystalline films are versatile relative to those avalible to flat aromatics,and,consequently,their charge transport properties in organic materials-based devices can be improved.In addition,the nonplanar structures provide concave surfaces that recognize the convex surfaces of fullerens.This mode of self-assembly makes them useful in creating atomically defined p-n junctions in organic photovoltaics.Finally,these materials are more soluble and less likely to spontaneously aggregate compared to flat aromatics,allowing for solution-based processing of materials.This paper is based on a series of research work of contorted hexabenzocoronene(c-HBC),which is discussed from the following three major aspects:(1)We have designed and synthesized three substituents of c-HBCs,for example,containing dodecyloxy,bromo substituents and trimethylsilyl substituents.The introduction of dodecyloxy groups in HBC molecules is primarily intended to increase its solubility in conventional organic solvents;The introduction of the bromine substituent is mainly due to the fact that the bromine atom is both a easy leaving group and a reactive site for various coupling reactions;However,inttoducing of trimethylsilyl such a substituent is mainly due to its easy to leave and can be in the four-substituted HBC on the expected reaction to get the desired material.(2)The propynyl group reaction was carried out on a bromine-substituted HBC to give a propynyl-substituted HBC;And then the alkyne metathesis reaction will be gone,a single HBC molecules through carbon-carbon triple bond to form a large group of ? electrons conjugated system.(3)The tetrabromo-substituted HBC molecules produced nano-spherical oligomers by Yamamoto coupling reaction,and conducted a series of studies on the thermal stability,light absorption properties and spatial configuration of this material.