Design, Synthesis And Characterization Of Novel Organic Molecules Containing Nitrogen

Organic light-emitting materials have become one of current researching hotspots in the field of optoelectronic information functional materials because they have more advantages when comparing to inorganic light-emitting materials. Using triphenylamine and carbazole which have hole transport ability as important pieces, a series of novel organic light-emitting functional molecules were designed and synthesized and their optical properties were studied in this thesis. The main research work includes the following:In the first part, a series of pyrazoline compounds were synthesized and they were all characterized by 1H NMR, 13C NMR, and HRMS.We found that they all had good photochemical properties through a detailed study of their UV-visible absorption spectra and fluorescence emission spectra.Based on the density functional theory B3LYP method, the optimal configuration of these compounds have been studied, meanwhile, thermal and electrochemical analysis of these compounds have been carried out, the results indicated that these compounds had a high thermal stability and good redox. Because of the light-emitting and hole-transport function, these compounds can be used as doped luminescent materials with multi-functional characteristics.In the second part, terpyridine was connected to triphenylamine by vinyl through Wittig-Hornor reaction, and the compounds were all characterized by 1H NMR, 13C NMR, and HRMS. Through a detailed study of their UV-visible absorption spectra and fluorescence emission spectra,we found that their maximum UV absorption wavelengths were in the range of 350-450nm, and fluorescence emission wavelengths were in the range of 484-492 nm, which emit green light. Applying the density functional theory B3LYP method, the optimal configuration of these compounds have been studied, meanwhile, electrochemical analysis of these compounds have been carried out and the results showed that they had good photochemical properties. So with the light-emitting and hole-transport function, these compounds can be used as doped luminescent materials with multi-functional characteristics.Connecting different aromatic compounds to the azo molecules through Suzuki coupling reaction ,a series of azo compounds were produced in the third part. From the UV-visible absorption spectra, it can be seen that through the introduction of different groups (benzene, naphthalene, thiophene, carbazole, pyridine, etc.), considerable red shift of UV spectra would take place; also from the fluorescence spectra, we can see that fluorescence emission peak of these compounds appeared at about 715 nm.We also studied photochromic properties of these compounds with ultraviolet lamp at 365 nm, but apparent photoinduced color changing has not been found.