Synthesis And Properties Of Ullazine Derivatives Containing Diarylboron/Diarylamine Motif

Polycyclic aromatic hydrocarbons(PAHs)are an important class of organic compounds with excellent photoelectric properties.In recent years,heteroatom-doped polycyclic aromatic hydrocarbons have provided the possibility to adjust the properties of PAHs,which has attracted a lot of interests of researchers.Indolo[6,5,4,3-ija]quinoline,also known as Ullazine,are a new type of aza electron-rich PAHs.Ullazine,which is isoelectronic with pyrene,have been used as part of dyes in dye-sensitized solar cells and the charge transport materials of organic field effect transistor.On the other hand,both of triarylboron and triarylamine have excellent optoelectronic properties and have been widely applied in organic optoelectronics.This thesis is dedicated to the study of Ullazine derivatives containing diarylboron and/or diarylamine.We successfully synthesized a series of Ullazine derivatives containing diarylboron and/or diarylamine,and studied their optoelectronic properties sysmatically.Preliminary results indicated that some of them can be used in the field of anion sensor.The main contents are as follows:1,The research background of Ullazine and its derivatives are reviewed comprehensively,and the research advance of triarylboron and triarylamine are also briefly introduced.At the end of the first chapter,we proposed the idea of this thesis2,Ullazine derivatives with mono-diarylboron and mono-diarylamine were designed and synthesized successfully by two different synthetic routes.Photophysical properties were systematically investigated.Ullazine derivatives with mono-diarylboron can be used as anion sensor.Ullazine derivatives bearing mono-diarylamine shows different properties with Ullazine with mono-diarylboron,in specifically,have two sets of reversible redox peaks.3,Ullazine derivatives with multiple diarylboron and multiple diarylamines were successfully synthesized via several routes..Photophysical studies demonstrated that the Ullazines bearing diarylboron units showed moderate ICT character.The results demonstrated that the number and position of the diarylboron/diarylamine units have great impact on the photophysical properties of the resulting Ullazine-based PAHs.Overall,the photophysical properties suggest that Ullaizne-based triarylboron and triarylamine are promising candidateds for use in organic electronic materials.