Synthesis Of Schiff-base Porphyrins And Study Of Their Spectrum Properties

Porphyrin compounds had made many great progresses in the research and application of red Organic Electro-luminescence devices, because they have high red fluorescence. Now people often modify the Porphyrin compounds with nitrogen heterocycle or nitrogen arylcycle to get better luminescence performance. The Schiff base also have been called imine or imine substitute compounds, they are an kind of organic compounds that include C=N group. Schiff bases are easily synthesized, many kinds of amines and aldehyde or ketone with carbonyl group could be choosen to synthesize different schiff bases smartly. Through changing linked substitute and transforming donor function or position, many compounds with multivariate structure and function can be exploited. In this paper, we designed that we first synthesized 5-(4-aminopheny1)-10,15,20-triphenyl porphyrin, then through Schiff base introduced nitrogen arylcycle(Polyarylamine) and nitrogen heterocycle(pyrazole) to modify porphyrin to improve their luminescence performance and to reduce the difficulty of synthesis and purification. The main contents are as follows:1.The research progress of the porphyrins, Schiff base, Polyarylamine compounds and pyrazole compounds was briefly introduced, their research and application in Organic Electro-luminescence devices was introduced.2. Eight Schiff base porphyrins included four substituted phenyl Schiff base porphyrins, a pyrazole Schiff base porphyrin and three polyarylamine Schiff base porphyrins have been designed and synthesized. Preparation of these Schiff base porphyrins was carried out by condensation of these substituted aldehyde with 5-(4-aminopheny1)-10,15,20-triphenyl-porphyrin. The structures of all these compounds were characterized by 1HNMR, elemental analysis, IR spectra and mass spectra.3. The formylation reaction of pyrazole heterocyclic and Polyarylamine and the synthetic methods of Schiff base porphyrins have been also discussed, by optimizing reaction condition, we could get high yield of target products in formylation reaction.4. The Uv-Vis spectra and fluorescence spectra of eight Schiff base porphyrins were tested and compared with the TPPH2. Red fluorescence emission of these porphyrins was observed in fluorescence spectra. we found that the Schiff base porphyrin introduced the substituent with pyrazole heterocyclic or Polyarylamine through Schiff base had better luminance than other Schiff-base Porphyrins, and the pyrazole heterocyclic Schiff base porphyrin had higher fluorescent quantum yield.5. Some explanations for these results were given based on the molecular structures of Schiff base porphyrins.