| Polycyclic aromatic hydrocarbons（PAHs）, considered as a small segment of graphene, have attracted intensive interests owing to their potential applications in organic optoelectronics such as field-effect transistors and photovoltaic cells. One distinct advantage of organic functional materials is that their properties can be readily tuned by precise modification of their structures. Chemical doping of heteroatoms to the lattice of aromatics is an effective strategy to modulate their intrinsic physicochemical properties. Coronene is a disc-shaped nanographene with zigzag periphery which possesses intriguing D6 h symmetry and perfect delocalization of aromaticity. Coronene and its derivatives have been broadly applied in many fields. This dissertation focuses on the synthesis and property stud y of nitrogen or azaborine-doped coronenes and their derivatives.In the first part, a four-step synthesis of C3-symmetric parent 1,5,9-triazacoronene（TAC） and its derivatives was firstly achieved from inexpensive starting material. In addition to routine characterization, their crystal structures, photoelectrical properties and thermal stability were also studied experimentally and theoretically by DFT calculations. It was revealed that the azacoronene cores were perfectly co-planar and the crystal adopted a dense face-to-face π-π stacking which is favorable for charge transportation.In the second part, a novel BN-doped coronene and its derivatives have been successfully synthesized in one step from triphenylene-1,5,9-triamine. Their crystal structures, photoelectrical properties and thermal stability were studied experimentally. The peripheral C-H bonds of the NB-doped coronenes were reserved which allows functionalization to tune their properties. We have successfully introduced substitutions to these compounds for further functionalization. |
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