Synthesis,Properties And Application Of BN-doped Perylene-Type Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic hydrocarbons(PAHs)have unique electronic structure and photophysical properties,which are widely utilized in biomedicine,organic photoelectric materials and related fields.However,research on boron-nitrogen doped polycyclic aromatic hydrocarbons is relatively limited,due their complicated and difficult synthesis.This thesis aims to develop new synthesis routes and enrich the family of boron-nitrogen doped PAHs.The main research content is as follows:In the first part of this thesis,we reviewed the latest research progress of boronnitrogen doped PAHs,perylene-type PAHs,coronene-type PAHs,and proposed the research ideas for the thesis.In the second part of this thesis,using 1-bromo-2-nitrobenzene and 2-bromoaniline as precursors,we successfully synthesized a class of bis-BN fused perylenes(BNMes,BNMe,BNPh and BNOH)through sequence of cross coupling reaction,Wohl-Aue reaction,reduction reaction,substitution reaction,Stille coupling reaction and electrophilic borylation reaction.Photophysical studied showed that the absorption and emission spectra of BNMes are redshift compared to BNMe.Density Functional Theory(DFT)calculations show that the introduction of BN units reduces the HOMO energy level of BN-perylene and increases the LUMO energy level,resulting widen HOMO-LUMO energy gap.At the same time,we successfully obtained the single crystal X-ray structure of BNMes through solvent diffusion method.In addition,thermogravimetric analysis shown highest stability of BNMes.Finally,we employing BNMes as the emitting layer,we fabricated a blue emitting Organic Light Emitting Diode,further expanding the application of BN-perylene type PAHs.In the third part of this thesis,we designed six different routes attempt to synthesize BN-coronene.Although we were unable to successfully synthesize BNcoronene,we successfully synthesize a phenazine compounds,and increased the yield of phenazine precursor compounds from 5% to 52.1%.In summary,this thesis focuses on the design,synthesis,property study,and application of novel BN-doped PAHs,providing experimental basis for the future application of BN-PAHs as optoelectronic materials.