Synthesis And Spectrum Properties Of Meso-1,3,4-Oxadiazole Substituted Porphyrins

Porphyrin macrocycle compounds are widely studied as materials of red luminescence devices because of the light-emitting wavelength not only lies in red-light district but also has excellent emission in narrow band etc.Hence, they have became a hotspot science issue of luminescence materials.The devices always show high color purity,but the fault is low brightness,inefficiency and self-aggregation.2,5-disubstituted-1,3,4-oxadiazole compounds are a important kind of blue dye.Their merits lies excellent thermodynamics stability,charge transmission, high electron affinity, well filmed, antioxidation an so on. At the same time, the luminescence properties will be improved if disubstituted by aromatic structure groups. In this thesis, a series of Meso-disubstituted porphyrin macrocycle compounds with D-A model are synthesized, characterized. Meanwhile, solvent effect is used in the study of intramolecular charge transfer (ICT) properties. The luminescence properties and fluorescence quantum yields of these six kinds of porphyrin compounds are improved. The fluorescence properties show solvent dependant, especially for the three-part system compounds PTO and POT that with 1,3,4-oxadiazole(OXD) group and triphenylamine(TPA) group, showing typical intramolecular charge transfer (ICT) properties.The main contents of this thesis are as follows:1. The synthesis and application of the porphyrins,1,3,4-oxadiazole compounds, some spectra parameters present in the thesis, and general research methods of spectrum were briefly introduced.2. Six kinds of new prophyrins, including five Meso-monosubstituted oxadiazole porphyrin compounds and one kind of Meso-tetrasubstituted oxadiazole porphyrin compounds have been designed and synthesized. Because of the difference properties of the compounds, different routes, including Vilsmeier-Haack reacation have been used to get five kinds of different substituted-1,3,4-oxadiazole compounds. Hence, different prophyrins are synthesized respectively. The structures of all these porphyrins were characterized by 1H NMR, UV spectra and mass spectra.The mechanizations of these reacations are discussed deeply. The synthetic methods have been discussed and optimized.3. The UV spectra and fluorescence spectra of six porphyrins were tested. The relationship between molecular structure and the spectral properties, solvent effect, were scientifically discussed.Because some kinds of D-A model molecule structure show intramolecular charge transfer (ICT) properties, two kinds of three-part system porphyrins(POT and PTO) present ICT properties, showing special "Dual Fluorescence". With Lippert-Mataga plot, ICT properties have been studied deeply. Meanwhile, all these prophyrins compounds have higher fluorescence quantum yields than the reference compound TPP. Therefore, they may have potential application as novel fluorescence material.